Boston October Events

What to Do & See

Boston Events for October 2020

Top Things to Do & See in Boston during October

The Boston Events Calendar for October 2020 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.

Please note:  Some of the events and activities on this page may be impacted by the ongoing coronavirus pandemic.  Stay tuned for updates - and stay flexible! 

With The Lion King at the Boston Opera House, Rent at the Shubert Theatre, and SpongeBob: The Musical at the Wang Theatre, October is an especially exciting month for theater fans.   (Please note:  There may be some schedule changes due to the coronavirus pandemic.)

Concert fans can catch The Killers at TD Garden and more top acts.

Fall foliage colors appear in early October, and they are looking brilliant so far (possibly due to the late-summer drought) - 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 2020

Theater productions and shows for October in Boston

Top October Theater Shows in Boston

Although most Boston theaters remain closed through the first half of October, the Wilbur Theatre will reopen on October 16.

Schedules & Tickets

TicketNetwork Discount Code - Enter TNTIX to get $10 off orders of $300+

Shows for October 

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.

Fall Foliage Cruises from Boston

Fall foliage along the New Hampshire Coast

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

Boston Concerts & Shows - October  2020

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

Schedules & Tickets:

TicketNetwork Discount Code - Enter TNTIX to get $10 off orders of $300+

More Concerts & Shows for October

Boston Concerts & Shows throughout the Year  

Visit Cape Cod on the Fast Ferry in Early October

Cape Cod tour from Boston

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

Boston Columbus Day Weekend Events

Marchers in Boston's Columbus Day Parade

Dates for Columbus Day Weekend:  Saturday, October 10; Sunday, October 11; Monday, October 12

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 - Cancelled

Christopher Columbus statue in Boston's North End

When:  Monday, October 3, 12 noon - 4pm  
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 a magician, storyteller, bubbles, and aquarium tidal pool, and a musical petting zoo to celebrate Boston's Italian heritage and the Columbus Day holiday in this gorgeous park overlooking Boston Harbor.

Cape Ann Artisans Open Studios - 2020

Photo of painting by Rob Diebboll, Rockport, MA

Don't miss this wonderful excuse to tour artist studios along the beautiful Rockport and Gloucester coast on Columbus Day weekend!  19 artists and artisans will welcome you to view their paintings, sculpture, mosaics, photography, 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 10 and 11, 10am - 5pm
Where:  Open Studio Tour map and more information at  You can also 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 bright magenta Studio Tour banner at each location
More information:  978-546-6186; Cape Ann Artisans website:
Cost:  Free
Painting in photo: "The Next Wave" by Cape Ann painter Rob Diebboll, 1 Camborne Way, Rockport 
More Columbus Day Events in and near Boston

Columbus Day Parade 2020

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.

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

Please note:  Due to the coronavirus pandemic, the parade may not take place or may be modified this year; we will post updates as soon as we receive them.

When:  Sunday, October 11, approximately 1pm - normally lasts about 2 hours
Where:  East Boston for 2020
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

HUBweek - Celebrating Innovation in Boston - Cancelled for 2020

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:

John Coltrane Memorial Concert - Not scheduled

The 43rd Annual John Coltrane Memorial Concert would have taken place this year - but it is not scheduled due to the coronavirus pandemic.  Fingers crossed for next year.

Tickets:  normally $25-$40

Find more Boston Concerts during October

Boston International Antiquarian Book Fair - 2020 - VIRTUAL

When:  September 29-30 (Dealer to Dealer portion); 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
General public entrance fee:  $TBD for Friday night preview; free on Saturday and Sunday

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 (in future years; not in 2020), 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 - Postponed to 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 free cupcakes, with fun activities for all ages all day.

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:  Monday, October 11, 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 2020 - VIRTUAL

Photo of HONK Festival band - coming to Boston on Columbus Day Weekend

When: October 10-11
  Davis Square, Somerville; Harvard Square, Cambridge (normally - but this year HONK! will be virtual, bigger than ever, and virtual)
Cost:   Free 
More information:

HONK!  will be virtual this year.  Check the event website ( for details and updates.

This information applies to normal years, in case you're planning ahead for next year:

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.  Participants come from around the U.S. and other parts of the world.  Expect to hear a cacaphony of sounds reminiscent of New Orleans brass bands, European Klezmer, Brazilian-Afro music, Romani and Balkan music, and much more.

The 3-day fest is packed with events and activities, and is bigger and better than ever this year.  Find out about all events here:

Head of the Charles Regatta - 2020

Head of Charles rowers

When:  October 17 and 18, 8am - 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)

Please note:  Due to the coronavirus pandemic, the Head of the Charles Regatta will take place this year as a remote event.  For details about how to participate and/or watch, please see the event website.

For more information, including best viewing spots and hotels:  Head of the Charles Regatta

More than 11,000 elite athletes from around the world compete in 55 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 - Virtual for 2020

Boston Book Festival event information

When:  October 4 - 25 - 100% virtual for 2020
Cost:  Free
More information including schedule & locations:  website

A huge lineup of 150+ renowned and mostly local writers, scholars, NPR hosts, publishers, and thought leaders including National Book Award, Newbury, and Pulitzer Prize winners converge in dozens of forums, presentations, and discussions organized around topics such as "Graphic Memoirs" and "Pathogens and Pills" to celebrate our local culture of reading and ideas, making the Boston Book Festival the largest literary event in New England. 

Featured speakers include Oneeka Williams, Natasha Trethewey, Sophie Yanow, Jason Chin, Chryl N. Laird, Derrick Barnes, Jacob Kramer, K-Fai Steele, and Brad Aronson - plus many more!

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.

Boston Halloween Pumpkin Float - CANCELLED

Boston Halloween Parade and Pumpkin Festival

Cancelled due to the coronavirus pandemic.  We're leaving this information up in case you're planning 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

Fort Point Open Studios 2020 - VIRTUAL Event

Fort Point Open Studio exhibit
Fort Point Open Studio exhibit

Oct 16 Preview from 4pm-7pm
       Oct 18 and 19 from 12 noon - 6pm

Virtual event due to the coronavirus pandemic.  Online festivities will include live artist talks and discussions, studio tours, workshops and demonstrations, performances, readings, docent tours, and LOTS of art.  Check the event website for details.

We're leaving this information up in case you're planning for 2021:

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.  Performances, free hands-on art-making activities, and other special events will also take place.

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  2020

New England Patriots at Gillette Stadium

Although two New England Patriots home games take place at Gillette Stadium during October, no decision about letting fans be present in the stadium has been made yet.

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

TicketNetwork Discount Code - Enter TNTIX to get $10 off orders of $300+

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 & Hockey at TD Garden for the Preseason & Regular 2020 Season - Currently TBD

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

Please note:  Due to the Coronavirus pandemic, the NHL 2020 season is still being determined.

At this time, the Bruins are not anticipated to play in October.

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

Best Fall Foliage Tours Departing from Boston - 2020

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 colors by mid-month. 

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

Celtics Basketball at TD Garden - 2020

 Boston Celtics playing at TD Garden

The Boston Celtics are no longer in the NBA finals.  Stay tuned for 2020 season details.

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

Museum of Science Exhibits - 2020

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

Special Exhibits at the Museum of Science

What I Eat: Around the World in 25 Diets - Now through June 30, 2020 - See similarities and differences in the ways diffferent cultures approach and consume food through these fantastic photos and stories - Free with museum admission.

Dogs!  A Science Tail - Feb 9 - June 30, 2020 - Understand the science behind why we love dogs, and understand how they see, hear, and smell the world - Free with museum admission.

Permanent Exhibits

With 29 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; occasional special closings occur
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

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

OctoberFest at Harpoon Brewery 

Harpoon Brewery in South Boston Waterfront

Harpoon Brewery's 24th annual German-style OctoberFest boasts 3 stages with live music, a big selection of Harpoon beers and ales, and lots of bratwurst and other German food sold by a local restaurant.  Come do some Chicken Dancing, keg bowling, and enjoy 3 stages filled with German Oompah bands at one of New England's largest OctoberFests.  

Try your luck at this year's new events: a German chocolate-eating contests!

When: (dates & times to be confirmed)
   - October 2 - 5:30pm - 11pm (doors close at 9:30pm)
   - October 3 - 1pm - 7pm (doors close at 5:30pm)
Where: 306 Northern Ave, South Boston Waterfront
Nearest T station: Red Line/South Station; take Silver Line 2 or 3 and get off at Harbor Street, or catch the free shuttle behind Federal Reserve building next to Fort Point Channel off Summer Street
Parking:  None at the Brewery - so catch the shuttle from South Station (Summer St going toward Fort Point Channel)
Cost:  $25 - includes one drink ticket and a souvenir cup (additional cost for food and additional drinks); bring a designated driver who will receive complimentary non-alcoholic beverages - or stay over in a nearby South Boston Waterfront hotels so that everybody can have fun).   General Admission tickets are not sold in advance - so pay at the door (cash only). You can also buy Early Access passes - see Harpoon's website for details.
Age:  21+, and you must have proper ID
More information:  Harpoon Brewery website

Boston Fashion Week

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

Boston Fashion Week is bigger and better than ever this year - 7 days packed with celebrations of Boston style.  Enjoy runway shows, exhibitions, special events such as GlamSlam, and parties as Boston's fashion professionals, retailers, and talented design students explore ideas, innovations, and new directions a venues throughout the city. 

  • When:  September 22-28
  • More information about how to participate, 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

Pru Boo Boston Halloween event at Prudential Center in October

When:  Sunday, October 27 - 11am-1pm.  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.  

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:

  • 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
  • Jazz Cruise on Northern Lights - Sunday evenings thru Oct 11- Enjoy live jazz music and dazzling city lights as you cruise around Boston Harbor past scenic attractions
  • Adirondack III Day Sail - Enjoy cool breezes and the afternoon sun on this relaxing sightseeing sail around Boston Harbor and the Inner Harbor Islands - Choose a 1.5 or 2 hour sail on this classic 80-foot pilot schooner
  • Boston Harbor Cruise on Northern Lights - thru Oct 25 - Soak up Boston's unique sites and rich history on this comfortable sightseeing cruise around the Harbor - perfect friends and family experience!  Drinks and small bites are available for purchase at the bar
  • Adirondack III Sunset Sail - Relax as the setting sun turns the sky brilliant colors during this calming sunset sailing experience - these sell out fast, so don't wait to book!
  • Northern Lights Sunset Cruise - Unwind on this popular after-work cruise as the sky changes brilliant colors and light music plays in the background.  Stop by the bar for a drink, watch the sights go by, and hear the USS Constitution's traditional sunset salute
  • City Lights Champagne Cruise on Northern Lights - Unwind with a glass of champagne as you gaze at Boston's sparkling skyline as relaxing music plays softly in the background on this after-dark cruise around the Harbor

Coming Soon:

  • 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
  • An Irish Christmas Carol Cruise - Get into the holiday spirit with Slainte, the Northern Lights' house Irish band.   Raise your glass and toast the holidays as you join in singing some merry Irish holiday ballads on this popular Harbor cruise - Book now
  • Cocoa & Carols Holiday Cruise - Sip hot chocolate and treats as the Blue Motion Quartet plays your favorite jazzy holiday music on this holiday cruise - Book now

Cranberry Harvest Festival on Columbus Day Weekend

Boston Cranberry Harvest Festival - Christopher Columbus Day Event

When:  October 11-12, 10am - 4pm, rain or shine
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

New England Coastal Tour from Boston

New England coastal tour from Boston

This day trip New England Coastal Tour gives you spectacular views of the beautiful New England coastline along Massachusetts, New Hampshire, and Maine. 

You'll get to visit historic Nubble Lighthouse, enjoy lunch and leisure time in quaint Kennebunkport, visit Hampton Beach, and see all the charming villages along the rocky coastline as you cruise along in a luxury climate-controlled coach. 

Boston hotel pickup and dropoff included.

Find out more

More Fun Boston Tours & Cruises

Salem Halloween:  Haunted Happenings Grand Parade

Salem MA Halloween Events

When:  Thursday, October 3, 6:30pm - 8:00pm
Location:  Downtown Salem, MA; ends at Salem Common

The Haunted Happenings Grand Parade officially kicks off the season of witches, ghosts, and goblins with a lavish pageant of costumes, music, 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.

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

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

Need a Boston Hotel?

Use this handy hotel map from to find the perfect place to stay.  Just enter your dates to find what's available, see the best rates, and make your reservations.