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
Enter DISCOVERY 10 to save 10% on TicketNetwork & TicketLiquidator tickets
- Rent - Wang Theatre - Oct 10-17
- Dead Can Dance - Wang Theatre - October 15
- RuPaul's Drag Race: Night of the Living Drag - Orpheum Theatre - October 15
- Frankie Valli - Wang Theatre - October 23
- Million Dollar Quartet - Shubert Theatre - Oct 29-30
- More Boston Theater District Shows in other months
- Where to have dinner in Boston's Theatre District
Need a Hotel or Short-Stay Apartment in Boston?
Enter your dates to see available hotels and rates. Click through to read reviews and make your reservations.
Booking.comMore about how to save on Boston hotels
Fall Foliage Cruises from Boston 2021
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
The Boston Marathon 2021
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
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:
- Northern Lights Sunset Cruise - Grab a drink from the bar and watch the sun set on this sail around the Harbor
- Fall Foliage Brunch Cruise on Northern Lights - Enjoy a tasty gourmet brunch, fall foliage, and panoramic views as you cruise around Boston Harbor
- Fall Foliage Lunch Cruise on Northern Lights - Sip hot cider as you enjoy lunch on this relaxing fall foliage cruise to celebrate seasonal colors
- Adirondack III Day Sail - Enjoy cool breezes on this sightseeing sail around Boston Harbor and the Inner Harbor Islands - Ends Oct 16
- Adirondack III Sunset Sail - Relax as the setting sun turns the sky brilliant colors during this calming sunset sailing experience - Ends Oct 16
- Brunch Cruise - Savor a delicious 3-course brunch on this relaxing sightseeing cruise around Boston Harbor
- Gift Card - Give the perfect gift!
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
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
Enter DISCOVERY 10 to save 10% on TicketNetwork & TicketLiquidator tickets
- John Legend - Orpheum Theatre - October 17
- Michael Buble - TD Garden - October 17
- Twenty One Pilots - Various venues - October 18, 19, 20, 23
- 10,000 Maniacs - City Winery - October 22
- Frankie Valli - Wang Theatre - October 23
- Gordon Lightfoot - Wilbur Theatre - October 24
- Harry Styles & Jenny Lewis - TD Garden - October 25
- Passenger - House of Blues - October 29
- The Killers - TD Garden - October 3, 2022
- Dead Can Dance - Wang Theatre - Postponed - Date TBD
Schedules & Tickets:
More Concerts & Shows for October
Boston Concerts & Shows throughout the Year
Visit Cape Cod on the Fast Ferry in Early 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
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:
- Day trip from Boston
- Newburyport/Rockport Commuter Rail from North Station
- Fast ferry from Boston's Long Wharf to Salem
- #450 bus from Haymarket Station in Boston
Check out Halloween in Salem for more about the witch museums.
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.
Boston Columbus Day Weekend Events 2021
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:
- Christopher Columbus Day Parade
- Cape Ann Artisans Open Studio
- Cranberry
Harvest Festiva
- HONK! Festival
- More about Boston Columbus Day Events
- More about the Columbus Day Parade
Columbus Park Fall Festival & Pumpkin Patch 2021
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
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 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
- More about the Boston Columbus Day Parade - Info, route, best places to watch, & photos
- More about other Columbus Day events
Where to Stay In or Near Boston's North End
More hotels in Boston's North End
Lawn on D
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
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
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
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
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
Combine a scenic fall foliage cruise around Boston Harbor with a delicious brunch or lunch on the elegant Yacht Northern Lights this month.
- Fall Foliage Brunch Cruise on Northern Lights - Enjoy a tasty gourmet brunch, fall foliage, and panoramic views as you cruise around Boston Harbor
- Fall Foliage Lunch Cruise on Northern Lights - Sip hot cider as you enjoy lunch on this relaxing fall foliage cruise to celebrate seasonal colors
Fort Point Open Studios - 2021
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.
- Visit chef-owned restaurants in Fort Point
- Where to stay: South Boston Waterfront Hotels
- More information: FPAC website
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
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!
Enter DISCOVERY 10 to save 10% on TicketNetwork & TicketLiquidator tickets
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
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:Enter DISCOVERY 10 to save 10% on TicketNetwork & TicketLiquidator 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):
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
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***
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
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
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.
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.
Museum of Science Exhibits - October 2021
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
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
Beacon Hill with a BOO!
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?
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
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
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 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
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
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
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
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
More Articles about Things to See & Do in Boston in October
- Interested in getting some exercise while you sightsee? Check out Boston bike tours
- Halloween in Boston - lots of fun things to do
- Fall is just around the corner - and now is a good time to start planning a breath-taking fall foliage cruise
More Fun Ways to See Boston
Need a Boston Hotel or Apartment?
Use this handy map from Booking.com to find the perfect place to stay. Just enter your dates to find what's available, see the best rates, and make your reservations.
Booking.com
