The Boston Events Calendar for October 2021 is packed with exciting events:  the huge Columbus Day Parade, Head of the Charles Regatta, Boston Fashion Week, and at the end of the month, Halloween events.

To add to October's exciting events, the Boston Marathon (rescheduled from April) will take place this year.

With an exciting lineup including new shows in the Theatre District, October is an especially exciting month for theater fans.

Music fans can catch shows at TD Garden, Big Night Live, House of Blues, Paradise Rock Club, and other top concert venues in Boston and Cambridge.

Fall foliage colors appear in earnest in early October, - so enjoy the gold and crimson leaves as they blaze across the city, and join one of the popular fall foliage tours and cruises.  

Go on the Fort Point Art Walk, take a sightseeing cruise on Boston Harbor, or just walk around one of the city's historic neighborhoods such as Beacon Hill and the South End, where jack-o-lanterns on doorsteps and our spooky Colonial-era graveyards will remind you Halloween is on its way.

Check out all our top recommendations for fun events & things to do in Boston in October - and plan your visit now!

Top photo: Beautiful October day in Boston's Back Bay neighborhood


Boston Theater & Shows for October 2021

Schedule & Tickets

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More shows for October 


Need a Hotel or Short-Stay Apartment in Boston?

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More about how to save on Boston hotels


Fall Foliage Cruises from Boston 2021

Fall foliage along the New Hampshire Coast
Lobster boats in Kennebunkport, Maine on a fall morning - Photo credit: iStock/DougLemke

Want to see gorgeous fall foliage along the New England and Eastern Canadian coastlines - and enjoy a few days relaxation and touring?  

Fall foliage cruises depart throughout October.  You can choose from day-long cruises and overnight trips.

When:  Departures throughout October
Cost:   Varies according to length of tour and cruise line
More information:  Fall foliage cruises

Find more cruises from Boston


The Boston Marathon 2021

Boston Marathon runners not far from Heartbreak Hill
Boston Marathon runners not far from Heartbreak Hill

The Boston Marathon - one of the city's biggest events of the year, and also known as the "Patriots Day Race" - features about 31,500 elite runners from around the world competing in a route made difficult by rolling terrain and features such as "Heartbreak Hill." 

Although this hugely popular event normally takes place in April, it has been rescheduled this year to Monday, October 11 on Columbus Day Weekend.

Start times are different this year, with the Professional Men division kicking off at 8:37 am and Professional Women at 8:45 am.  You can find a complete list of start times for each division here.

Although the winners in the Professional divisions typically complete the course in just over 2 hours, many participants are still running hours later.  You can watch from anywhere along the route.

More about the Boston Marathon

Hotels close to the Boston Marathon route

Best places to watch along the Marathon route


Boston Harbor Cruises -  October

Boston sailing and yacht cruises

Tour Boston by boat - the best way to see the city!   Check out these fun sightseeing, music, and entertainment Boston Harbor cruises on the Yacht Northern Lights and Schooner Adirondack III:

Fun Boston Harbor Cruises To Do Right Now:

Starting in November:

  • Cocoa & Carols Holiday Cruise - Sip hot chocolate and treats as you listen to jazzy holiday favorites on this festive cruise - Book now
  • Holiday Brunch Cruise - See historic sights and panoramic views around Boston Harbor with friends and family as you enjoy this relaxing cruise with brunch, hot chocolate, and holiday cheer - Book now
  • Holiday Sunset Cruise - Watch passing landmarks as soft music plays in the background and the sunset displays brilliant colors behind Boston's city skyline - Find out more
  • An Irish Christmas Carol Cruise - Get into the holiday spirit on the Northern Lights as you raise your glass and toast the holidays with festive holiday music playing in the background on this popular Harbor cruise - Book now

Boston Concerts & Shows - October 2021

Boston Concert Schedule - October
Jose Gonzalez and yMusic playing at Berklee Performance Center - Photo taken by Ben Stas and courtesy of digboston.com

All of Boston's music venues have finally reopened, and you'll find a phenomenal number of concerts and shows this month!

Top October Concerts in Boston

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Schedules & Tickets:

More Concerts & Shows for October

Boston Concerts & Shows throughout the Year  


Visit Cape Cod on the Fast Ferry in Early October

Provincetown beach in October
Provincetown beach in October

The easiest and fastest way to get to scenic Provincetown at the eastern tip of Cape Cod is on the "Fast Ferry" - a sleek and luxurious passenger-only catamaran that whisks you to this charming village in only 90 minutes.

Explore Provincetown's many art galleries, chic clothing boutiques, and picturesque lanes at your leisure.

Watch the sun set as you feast on clam chowder and a lobster roll at one of the many restaurants overlooking the water.

But don't wait too long - the Fast Ferry runs only through the Columbus Day weekend.

Get Your Fast Ferry Tickets to Provincetown

Find out more about visiting Provincetown


Salem Halloween:  Haunted Happenings Grand Parade - 2021

Salem MA Halloween Events

When:  Thursday, October 7, 6:30 pm - 8 pm
Location:  Downtown Salem, MA around Salem Common and along Hawthorne Boulevard and Essex, Central, and Charter Streets

The Haunted Happenings Grand Parade officially kicks off the season of witches, ghosts, and goblins with a lavish pageant of costumes, music, floats, and entertainment - but that's just the beginning of Salem's Halloween festivities. 

More about the Grand Parade and the "Witch City"

Best ways to get to Salem from Boston: 

Check out Halloween in Salem for more about the witch museums.

Where to stay in Salem

More to See & Do in Salem:


Boston Discount Passes for Attractions, Tours, Cruises

Why pay full price for top Boston attractions such as the New England Aquarium, Museum of Fine Arts, Plimouth Plantation, Salem Witch Tours, Boston Harbor Cruises, and much more?

Boston Discount Cards are the best deal in town.  Select Boston CityPass to see Boston's Top Attractions at a leisurely pace, or choose the GoBoston card (you pick how many days) to see almost 50 attractions, tours, cruises, and day trips.

Save BIG with Go Boston discount card
CityPASS Boston discount card at www.boston-discovery-guide.com

Boston Columbus Day Weekend Events 2021

Columbus Day parade in Boston's North End
Columbus Day parade in Boston's North End

Dates for Columbus Day Weekend:  Saturday, October 9; Sunday, October 10; Monday, October 11

The 3-day Columbus Day Weekend holiday packs in lots of fun events in and around Boston.  You'll find plenty to do all weekend - plus big Columbus Day sales in all the stores!

Boston Columbus Day events to check out:


Columbus Park Fall Festival & Pumpkin Patch 2021

Columbus Park in Boston's North End
Columbus Park in Boston's North End

When:  Saturday, October 23, 12 noon - 3pm  
Location:  Christopher Columbus Park, Boston's North End (100 Atlantic Ave - next to the Marriott Long Wharf Hotel)
Public Transportation:  Blue Line/Aquarium; about a 3 minute walk north on the Greenway
Cost:  Free

The Columbus Park Fall Festival features a children's parade through the park (watch it or join it), a variety of music and entertainment by local groups, plus family activities including lawn games, pumpkins, and balloon animals to celebrate Boston's Italian heritage and the Columbus Day holiday in this gorgeous park overlooking Boston Harbor. 

Wear your costume!


Cape Ann Artisans Open Studios 2021

Photo of painting by Rob Diebboll, Rockport, MA
Painting by Deb Schradieck at Rockport Open Studios

Don't miss this wonderful excuse to tour artist studios along the beautiful Rockport and Gloucester coast on Columbus Day weekend!  Fourteen artists and artisans will welcome you to view their paintings, sculpture, mosaics, photography, quilts, pottery, jewelry, and other wonderful creations. 

You can easily rent a car and drive up from Boston for the day - or spend the weekend and go for walks along the beach, dine on lobster dinners, and browse in local boutiques, galleries, and antique shops.  View Rockport Hotels

Open Studio Tour:  October 9 and 10 at 10am - 5pm
Where:  Open Studio Tour map and more information at www.capeannartisans.com - or pick up brochures with route maps at the Cape Ann Chamber of Commerce, the Rockport Information Booth on Rte 127, and at each studio.  Look for the Studio Tour banner at each location
More information:  978-546-6186; Cape Ann Artisans website: http://capeannartisans.com
Cost:  Free
More Columbus Day Events in and near Boston


Columbus Day Parade 2021

Boston's Columbus Day Parade marching up Hanover Street in the North End
Boston's Columbus Day Parade marching up Hanover Street in the North End

Boston's Columbus Day Parade honors Christopher Columbus and his explorations of the Americas, Boston's military commitments to freedom from Colonial times through today, and the city's Italian heritage.

PLEASE NOTE:  The Parade will not take place this year, but a special Heritage Day event will be scheduled - details coming soon!  We are leaving the parade information up on the website in case you want to plan for next year.

The parade alternates between the North End (odd years) and East Boston (even years).  

When:  Cancelled for 2021(but normally on the Sunday of Columbus Day Weekend)
Where:  East Boston for 2022
Closest T stations:
- North End:  Blue Line/Aquarium or Green Line/Haymarket
- East Boston:  Blue Line/Maverick


Where to Stay In or Near Boston's North End


More hotels in Boston's North End


Lawn on D

Lawn on D summer events

Lawn on D, a playground for adults (kids are welcome too but this is mostly an adult venue) located behind the Convention Center in the South Boston Waterfront, is where you'll find fun swings with LED lights and comfy seating, bocce and other games daily from 7am-11pm throughout October (except for when the Lawn closes for private events - always check before going).  However, concessions selling food and beverages end on October 3.

Another option in this area is to sample one of the many restaurants in the Seaport and Fort Point areas of the South Boston Waterfront.  For Boston Harbor views while you dine, visit a Seaport restaurant.  To try the creative cuisine of some of Boston's most innovative chefs, head to a Fort Point restaurant.


Boston International Antiquarian Book Fair 2021

When:  November 12-14 (General public portion; paid preview on Nov 12)
Where:   Virtual this year, due to the coronavirus pandemic
Closest T station: N/A
For more information: website - PLEASE NOTE:  The book fair will be virtual again this year
General public entrance fee:  $TBD for Friday night preview; free on Saturday and Sunday

Normally, this is what happens:  Whether you're a serious collector of old books, want to shop for a few holiday gifts, or just like to read, the huge Boston International Antiquarian Book Fair is a must-visit.  With over 150 dealers from the U.S. and Europe, the fair attracts visitors from around the world.  In addition to the rare, collectible, and antiquarian books on exhibit and for sale, you'll also find manuscripts, autographs, maps, atlases, modern first editions, and fine and decorative prints.  Do you think you already own a treasure?  Bring your own books, maps, and ephemera and get a free appraisal.

If you're coming from out of town, hotels near the Hynes include the Back Bay Hilton, the Mandarin Oriental Boston, the Colonnade, the Charlesmark, the Sheraton Boston, and the Lenox.


Opening Our Doors Day in Fenway 2021

Big arts celebration in Boston's Fenway for Columbus Day

Fenway Alliance presents "Opening Our Doors," Boston's biggest single day of FREE arts, cultural, and educational events when its members invite you to 60+ activities, performances, tours, music, and games from 10am - 4pm.  

Festivities start on the Mass Ave side of the Christian Science Plaza at the intersection of Huntington Ave and Mass Ave. The kick-off celebration features a Kids Parade with the Hot Tamale Brass Band, performances, and an art zone with fun activities for all ages all day. Don't miss the Open Studios at the Fenway Artist Building (30 Ipswitch Street), and a guided tour of the Back Bay Fens at 10am. 

Added plus:  Free admission to several top Fenway museums, including the Museum of Fine Arts, Isabella Stewart Gardner Museum, and the Mary Baker Eddy Library Mapparium.

When:  Saturday, October 9, 2021 
Where:  Multiple locations in Fenway
Cost:  Free
More information:  Fenway Alliance website - Complete events schedule for Boston's Fenway neighborhood


HONK! Street Music Festival on Columbus Day Weekend - 2021

Photo of HONK Festival band - coming to Boston on Columbus Day Weekend
HONK! musicians in Davis Square, Somerville

When: October 9
Where:
  Somerville, Cambridge, East Boston, the South End, and Roxbury
Cost:   Free 
More information:  www.honkfest.org

HONK! Festival of Activist Street Bands fills streets in Cambridge and Somerville with celebratory music, colorful attire, and lots of fun during Columbus Day weekend. 

The event will be different this year because of, you guessed it, Covid:  1 day only instead of 3, only 15 local bands instead of participants from around the U.S. and other parts of the world, and no parade.

But here's the biggest change, and it's a good one:  Instead of taking place only in Somerville, this year's performances will be decentralized and will happen in 5 communities in the Greater Boston areas.  Check their website for more specific details - updates are expected around October 1:  http://honkfest.org


Head of the Charles Regatta 2021

Head of Charles rowers
Head of the Charles

When:  October 22 (8am - 10:30am), 23 (7:45am - 5pm), and 24, (7:45am - 4:30pm)
Where:  Charles River between Boston and Cambridge, MA
Cost:   Free viewing from most locations.  Exceptions include Reunion Village ($10 for one day) and the Eliot Bridge Enclosure ($90 for one day or $150 for both; includes breakfast, lunch, and 2 free drinks)
For more information, including best viewing spots, hotels, transportation (& road closures):  Head of the Charles Regatta

More than 11,000 elite athletes from around the world compete in 60+ events as part of the Head of the Charles Regatta, an exciting 2-day rowing meet held on the Charles River during the last full weekend in October. 

If you're visiting Boston this weekend, join the more than 300,000 spectators watching from the bridges and banks of the Charles.  Fall foliage along the river is usually near peak on this weekend - so bring your camera!


Popular Boston Tours & Cruises


Boston Book Festival - 2021

Boston Book Festival event information

When:  October 16-23
Cost:
  Free
More information including events, schedules, & locations:  website

Although the event is mostly virtual again this year, there's a huge lineup of renowned and mostly local writers, scholars, NPR hosts, publishers, and thought leaders including National Book Award, Newbury, and Pulitzer Prize winners converge in numerous forums, presentations, and discussions organized around topics such as "Legacy of Slavery" and "Women Working It" to celebrate our local culture of reading and ideas, making the Boston Book Festival the largest literary event in New England. 

Featured speakers include Bob Woodward, Sandro Galea, Tracy K. Smith, Jelani M. Favors, Annette Gordon-Reed, Meghna Chakrabarti, Dominique Mielle, Tatiana Schlossberg, Stephanie Yue, and Jef Czekaj - plus many more!  There are even a few in-person events at local library branches, and the "Boston in 100 Words" flash fiction writing event at Trident Bookstore on Newbury Street - but they're also live-streamed in case you can't make it in person.

In addition to exhibitions, discussions, sessions for writers, and presentations, you'll normally find live music, booksellers, food, and kids/teen activities - but this year is obviously different so stock up on snacks, perhaps a glass of wine, and whatever else you need to make the live virtual programs extra enjoyable.

Boston Book Festival is one of the biggest book fests in the U.S. and there's nothing else quite like it, so don't miss it!


Fall Foliage Boston Harbor Cruises on the Northern Lights

Fall Foliage Boston Harbor Cruise on the Northern Lights
Boston Light on Little Brewster Island in Boston Harbor - the first lighthouse built in North America in 1716 and restored in 1783, after being destroyed by the British in 1776

Combine a scenic fall foliage cruise around Boston Harbor with a delicious brunch or lunch on the elegant Yacht Northern Lights this month.


Fort Point Open Studios - 2021

Fort Point Open Studio exhibit
Fort Point Open Studio exhibit

When:
Oct 15 Preview from 4pm-7pm
       Oct 16 and 17 from 12 noon - 6pm

Where:  Fort Point area of the South Boston Waterfront
Nearest T station: Red Line/South Station; walk across the Congress Street bridge
Parking: Free, in the Central Parking Lot at Binford and A Street
Cost:  Free...unless you buy some art!
More information:  Fort Point Arts Community website; 617-423-4299

Stop by the FPAC Gallery at 300 Congress Street, pick up a map showing the more than 150 open studios in 14 buildings, plus studios and pop-up venues (please note: some studios are open by appointment only this year and others will not be open).  Check out the public are on display at these and other locations:  A Street under Summer Street and at 300 Summer Street, Fort Point Channel, Boston Harborwalk, 5 Necco Street, A Street fence, Wormwood Park, Barlow's Park.

Then stroll around this area of former warehouses and explore the art studios, chat with the artists, and if you're unable to resist, buy a piece or two of memorable art from some of the area's emerging or well-known artists. 

Photo of painting by Karen McFeaters


Fun Boston Tours for October



More:   Sightseeing Tours   |   Tours for Teens   |   Kids & Family Tours


New England Patriots at Gillette Stadium - October 

New England Patriots at Gillette Stadium

Although two New England Patriots home games take place at Gillette Stadium during October,

Get your tickets now, and get ready to join in the fun!

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Where: Gillette Stadium
Getting there:
The Patriot Train - plus more ways to get to Gillette from Boston
Where to stay:  Hotels near Gillette Stadium
More Patriots tickets: Check for great prices & great seats


Bruins on the Ice at TD Garden - Preseason & Regular Season Games - October 2021

New England Bruins October schedule at TD Garden in Boston
Photo courtesy of Dan4th Nicholas

Preseason games start in early October, followed by the kickoff of regular season games.  Will this be the year the Bruins win another Stanley Cup?

See the Schedule & Get Your Tickets Now

Save when you use these Ticket Discount Codes:

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Find more Bruins tickets


Get Your Bruins Hoodie


Hotels near TD Garden

If you're coming to an event at the Garden, spend the night or the weekend at one of the nearby hotels, such as the stylish Boxer (shown in photo):

Boxer Hotel, top choice near Boston's TD Garden

More top hotels near the Garden:

Check out more hotels near TD Garden


Celtics on their Home Court at TD Garden -  November Schedule & Tickets 2021

 Boston Celtics playing at TD Garden

Get your Boston Celtics tickets for November home games, and head over to TD Garden for some fast action on the court.

The Garden's convenient location next to North Station makes it super-easy to get to.

Get ready for plenty of action at the net from Boston's champion basketball team.

Get your tickets now:**y-tickets-discount-code-tl-ace-tn.shtml***

Find more Celtics tickets

Where: TD Garden
Nearest public transportation: 
Green Line/Orange Line or Commuter Rail to North Station, next to the Garden
Where to stay:  Hotels near TD Garden


Best Fall Foliage Tours Departing from Boston - 2021

Boston fall foliage tours and cruises

Leaves may still be mostly green in Boston in October, at least during the first couple of weeks - so if you want to see gorgeous foliage, head outside of the city where you'll start to see lots of spectacular New England fall colors. 

These luxury 1-day fall foliage tours take you to the best viewing locations in New Hampshire, Maine, and Cape Cod.  Sit back and relax while someone else drives and you get to enjoy all the scenery!

More about fall foliage tours leaving from Boston



Enjoy Fall Foliage near Your Boston Hotel

Want to enjoy brilliant fall colors right in the city?  Boston is filled with trees.  Here's where to find colorful autumn foliage near these popular hotels:

Colonnade Hotel - Walk across Huntington Ave to Christian Science Plaza.  Find a comfortable bench by the reflecting pool, and enjoy the golden leaves on nearby trees.

Verb Hotel - Cross Boylston Street and enter The Fens, where you'll find the famous Victory Gardens and Kelleher Rose Gardens.

Charlesmark Hotel - Walk half a block to Copley Square.  Soak up some sun by the pool, explore the weekly Farmer's Market, and tour Trinity Church.

Four Seasons Hotel - Cross Boylston Street and enter Boston's Victorian-era Public Garden.  Admire the spectacular autumn colors and visit the  Make Way for Duckling statues. 

More places to see gorgeous autumn colors in Boston


Tours & Cruises to see Fall Foliage in Boston . . . and Beyond


New England Coastal Tour from Boston

New England coastal tour from Boston

This New England Coastal All-Day Tour gives you spectacular views of the beautiful New England coastline along Massachusetts, New Hampshire, and Maine.  By October, foliage should be brilliant along the way.

You'll get to visit historic Nubble Lighthouse in York, Maine, enjoy lunch, shopping, and leisure time in quaint Kennebunkport, admire the well-preserved 18th and 19th century architecture in quaint Kenebunk Village, visit Hampton Beach (after Labor Day, you may just drive by Hampton Beach and visit Stonewall Kitchen instead), and see all the charming villages along the rocky coastline as you cruise along in a luxury climate-controlled coach. 

Pickup and dropoff from selected Boston hotels is included.

Find out more


More Fun Boston Tours


Save Big $$$s on Boston Museums and More Top Attractions

Find out how a Boston Discount Card gives you free entrance to museums and lots of other attractions every day while your card is valid - plus you get to go straight to the head of the line.

Save BIG with Go Boston discount card
CityPASS Boston discount card at www.boston-discovery-guide.com

Museum of Science Exhibits - October 2021

Museum of Science Boston Exhibit
Museum of Science Butterfly Garden - Photo credit: Ted

Special Exhibits

Arctic Adventure:  Exploring with Technology - Find an Arctic fox, travel across a glacier, & more in this immersive exhibit

Science Behind Pixar:  See how art and science create magic

Design Engineering Workshop - Design, build, and test solutions for everyday problems

Permanent Exhibits

With fascinating permanent exhibits for all ages, there's always something to see, do, and learn.  Here are just a few of the most popular:  Butterfly Garden (extra fee), Colossal Fossil: Triceratops Cliff, Cosmic Light, Dinosaurs, Hall of Human Life, Live Animal Care Center, Mathematica, Nanotechnology, Natural Mysteries, New England Habitats, The Light House - plus 17 more!

Where:   Boston's Museum of Science
When:   Daily, 9am-5pm; open until 9pm on Fridays
Admission:  $29 general museum admission ($24 for kids).  Buy online to skip the line.  Get free museum admission when you have a GoBoston Discount card or Boston CityPASS card. 
Imax Theater and Planetarium:  Additional fees apply


Fun Events & Activities on the Rose Kennedy Greenway 2021

Splash fountain on the Greenway
Splash fountain on the Greenway

Weekly events on the Rose Kennedy Greenway begin to wind down in October, but there's still plenty to do and see as leaves begin to turn gold and crimsom.

  • Greenway Food Trucks:   Over 35 trucks offering specialties ranging from Korean to Summer Shack's seafood to frozen hoagies in Dewey Square, Congress Street, the Carousel, Rings Fountain (Milk Street), State Street, and Rowes Wharf Plaza, and Trillium Beer Garden.  You'll find them at 2-6 locations each day, and although the number of trucks vary each day, the number of locations and trucks is the biggest on Thursdays.
  • Farmers Market in Dewey Square run by Boston Public Market offering fresh produce, meat, cheese, breads and pastries, ice cream, and more.  Open Tuesdays and Thursdays 11am - 4pm
  • Boston Calling Block Parties - Live music and drinks from Blue Moon Brewing, Vizzy Hard Seltzer Canada, Topop Chico Aqua Mineral, and more.  Thursdays, 5pm-8pm, Dewey Square.
  • Trillium Beer Garden in the Wharf District Parks (High Street and Atlantic Ave) featuring draft beers by Trillium Brewing Company and a rotating selection of onsite food trucks.  Open Thursday and Friday 2-10pm, Sat 12 noon-10pm, Sunday 12 noon-6pm.
  • City Winery Open Air Wine Garden on Dewey Square across from South Station, serving their locally-crafted wine on tap plus with craft beer and cider by Harpoon Brewery along with a menu of fresh wraps, cheese boards, and snacks.  Open Wed and Thurs 4-9pm, Friday 4-10pm, Sat. 1-9pm, Sunday 11am-7pm.
  • Public Art - See new installations by Daniel Gordon in the Fort Point Channel Park
  • Fountains - You'll find them in 7 different locations along the Greenway.
  • Carousel - Open daily, 11am-8pm.  Tickets: $4.
  • Greenway Fitness Programs:  Free fitness and yoga classes from local studios; must preregister

More about the Rose Kennedy Greenway

Greenway walking tour and map


Beacon Hill with a BOO! 

Haunted walking tour for Halloween in  Boston's Beacon Hill

Murders, mysteries, mayhem, and the occasional ghost haunt this special 90-minute walking tour of Beacon Hill featuring (mostly) true tales.  Your guide for this ghoulish annual event, a volunteer with local tour group Boston by Foot, will show you the dark side and even darker alleys of this charming neighborhood.  Wear comfortable walking shoes and your favorite costume!

When:   6pm on October 31, Beacon Hill, Boston - arrive 10 minutes before tour starts 
Where:  Boston's Beacon Hill neighborhood
For more information:   Boston by Foot website
Cost:  $20 ($10 for Boston by Foot members) -  Purchase tour tickets directly from your guide - no reservations are required.  Interested in a private tour?  Boston by Foot will arrange that for you, at private tour rates, given enough lead time - call them at 617-367-2345 for details.

Can't make the Halloween tour? Catch Boston by Foot's "The Dark Side of Boston" tour and hear tales of crime, disease, death, and disaster as you walk around the North End.  Takes place earlier in October and throughout the year - check BBF's website for details.


Not Sure about Boston Neighborhood Locations?

Map of Boston showing central neighborhoods

This neighborhood map should help you get oriented. You can find a list of top attractions in each neighborhood here.

Need a more details?  See our recommendations for free and low-cost Boston maps.


2 Easy Ways to Save BIG in Boston on Tours, Cruises, Admissions

Boston Discount Cards offer you an easy way to save BIG when you take a Boston Harbor cruise or Duck Boat tour, visit Plimouth Plantation, the New England Aquarium, Museum of Science, Museum of Fine Arts, Fenway Park Tour, and more.  
Find out which Boston Discount Card is best for you.


Halloween Pet Parade & Costume Contest

Halloween Pet Parade

Does your pet love to dress up and strut around?  If so, bring out your favorite (pet) Halloween costume and head over to Faneuil Hall Marketplace on October 26 from 12 noon to 2pm to show off your holiday spirit. 

The Pet Parade takes place at 1pm.  At 2pm, your pet could win a prize.  Categories include Best Owner and Pet Combo, Best Local Boston Representation, and Most Creative.  Registration is required for this free event:  Faneuil Marketplace website

More Halloween Events in Boston


Octoberfests in Boston 2021

Harpoon Brewery in South Boston Waterfront

Three important things to know about Oktoberfests in Boston:  1) Contrary to what the name "Oktoberfest" leads you to believe, most happenin late September just a few in October; 2) as Boston's craft brewery scene expands, so does the number of Oktoberfests across the city; and 3) they're a lot of fun! 

Oh, and you should also know:  you must be 21+ and show ID to attend.

Here are the best Oktoberfests in and near Boston taking place in October where you can enjoy German-style pretzels, sausages, oompah music, dancing, and steins filled with your favorite seasonal beers on draft:

Harpoon Brewery 

What to enjoy:   Chicken dancing, live music, a big selection of Harpoon beers and ales, and lots of bratwurst and other German food
Where: 306 Northern Ave, South Boston Waterfront
When: 
   - October 1 - 6pm - 11pm
   - October 2 - 12 noon - 7pm
Tickets: $35-$49
More information:  Harpoon Brewery website

Aeronaut Brewing Company (Aeronaut Allston location)

What to enjoy:   German-inspired beers and food including sausage and pretzels plus oompah music
Where: 267 Western Ave, Boston's Allston neighborhood
When:  October 2, 1pm-9pm
More information:  Aeronaut website

Blackmoor Bar & Kitchen

What to enjoy:   Live music from the Yankee Strudel Band and Hofbrau Spieler Band from 2pm-9pm, German food from 2pm - midnight, and a large selection of German beer at this craft beer gastro pub
Where: 1 Chelsea Street, Charlestown (on the Freedom Trail)
When:  October 16, 2pm-midnight
More information:  Blackmoor Bar website


Boston Fashion Week 2021

Boston Fashion Week
Photo courtesy Boston Fashion Week Facebook - Graciela Rivas Collection Model Club Inc.

Boston Fashion Week breaks new ground this year by being the first public AR - that's Augmented Reality - art installation that's also a city-wide fashion exhibit featuring the work of regional fashion designers, photographers, textile artists, fashion schools, fanshion archives, and more.  To access it, all you have to do in install an app on your smartphone - plus a few designers will also host safe in-person events. 

  • When:  September 3-9
  • More information about how to download the AR app, plus a list of events, participants, and venues:   Boston Fashion Week's website.

Pumpkin Pageant & Costumed Dog Parade

Create the most fantastic pumpkin you can imagine, and compete to win the title for Funniest, Scariest, Most Original, and Overall Crowd Favorite. 

The mostly-free Pumpkin Pagent and Dog Costume Parade ($10 to enter your dog in the parade) takes place on October 27, 12 noon - 3pm at the Atlantic Wharf Waterfront Plaza in Fort Point, and includes lots of other fun - pumpkin carving for kids, face painting, DJ Magic Mic, locally-made bites, beer and wine (21+, at your own expense), & more.

See details:  Friends of Fort Point website


Pru Boo at Prudential Center - To Be Confirmed

Pru Boo Boston Halloween event at Prudential Center in October

When:  Sunday, October 24 - 11am-1pm (to be confirmed).  There's also a kids concert at 1:30 in the South Garden, weather permitting.  In case of rain, the concert will be in Pru Center's Belvidere Pavilion
Where:  Prudential Center
Cost:   $5 donation per child (12 and under) - purchase trick or treat bag at Customer Service desk starting Oct 1 or check in at the Food Court or Center Court as early as 9am on the date of the event to beat the crowds and pick up a map of all the activities.  Parking for the day will be $18 (Pru Center Garage).  Donations this year will benefit The Home for Little Wanderers.  You'll also find lots of non-food treats this year.
More information:  Halloween in Boston

Every year, over 50 stores and restaurants at the Shops at Prudential Center sponsor Trick or Treating for Charity,with proceeds going to a non-profit partner to benefit the neediest babies and children in Boston.  Kids come dressed in their cutest Halloween outfits and enjoy trick-or-treating, face painting, magic shows, pumpkin decorating, and more, but most important:  they'll be helping other children.  


Cranberry Harvest Festival on Columbus Day Weekend - Not Scheduled for 2021

Boston Cranberry Harvest Festival - Christopher Columbus Day Event

When:  Not in 2021
Location:  A.D. Makepeace Company, 158 Tihonet Road, Wareham, MA
Admission:  $10 adults, $5 seniors, free for children under 7 and military; free parking; some activities have additional fees or donations to the non-profit organizations that sponsor them
More information: Festival website or call 508-322-4000

Celebrate the fall cranberry harvest season at this annual Cranberry Harvest Festival open house, located at the nation's largest cranberry grower south of Boston.  This popular event attracted over 32,000 visitors last year.  Cranberry bog tours, family-oriented games and entertainment, and fresh cranberries to buy! 

More about the Cranberry Harvest Festival and nearby Plimouth Plantation and Mayflower II


More Fun Boston Tours & Cruises


Boston Halloween Pumpkin Float - Cancelled for 2021

Boston Halloween Parade and Pumpkin Festival

Put on your Halloween costume and head over to Boston Common's Frog Pond on Sunday, October 17 for a Halloween Pumpkin Festival, refreshments, music, and lots of family activities.  Halloween costumes are encouraged!  This free event takes place from 5-8pm.    

Bring an 8 inch or smaller hollowed out carved pumpkin - it will be lit and then floated on Frog Pond for a spectacular display from the glowing pumpkin luminaries.   (Note:  You MUST hollow it out - otherwise, it will not float!)

More information:  Boston Frog Pond website


HUBweek - Celebrating Innovation in Boston - Cancelled for 2021

Fall Foliage Boston Harbor Cruise on the Northern Lights
Artist painting one of the shipping containers used for HUBweek exhibits on City Hall Plaza; in the background, you can see a celebration of the Republic of China's National Day

HUBweek brings together innovators from all over the world for a festival celebrating cutting edge and impacful ideals in art and technology. 

Access to most exhibits, demonstrations, and nightly parties is free (although you must register); the concurrent file festival and Changemaker conference requires ticket.

Dates:  October 1-3
Locations:   Boston's Seaport and other venues around Boston
Event schedule and registration:  https://www.hubweek.org


More to Do in Boston in October

Events and things to do in Boston in October


More Articles about Things to See & Do in Boston in October



More Fun Ways to See Boston


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