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
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+
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.
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
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 www.capeannartisans.com. 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: http://capeannartisans.com 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 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
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.
Opening Our Doors Day in Fenway - Postponed to 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 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
When: October 10-11
Where: Davis Square, Somerville; Harvard Square, Cambridge (normally - but this year HONK! will be virtual, bigger than ever, and virtual) Cost: Free More information: www.honkfest.org
HONK! will be virtual this year. Check the event website (https://honkfest.org/) 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: http://honkfest.org
Head of the Charles Regatta - 2020
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.
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
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
Combine a scenic fall foliage cruise around Boston Harbor with a delicious brunch or lunch on the elegant Yacht Northern Lights this month.
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!)
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.
Best Fall Foliage Tours Departing from Boston - 2020
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!
The Boston Celtics are no longer in the NBA finals. Stay tuned for 2020 season details.
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.
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 - 2020
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.
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!
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.
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
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 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.
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.
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
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:
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
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
Cranberry Harvest Festival on Columbus Day Weekend
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!
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.
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.
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.