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.
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.
Concert fans can catch Fleetwood Mac and Bob Seger & the Silver Bullet Band at TD Garden, Little Feat and Steely Dan at the Orpheum, and plenty more top acts.
Fall foliage colors start appearing in early October - so enjoy the gold and crimson leaves as they light up 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
Get ready to be dazzled by a trio of Broadway hits during October: The Lion King, SpongeBob: the Musical and Rent.
Salem Horror Fest @ Salem Maritime National Historic Center - Goldstar $5, Full price, $10
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)
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 in Copley Square & Roxbury
When: October 17 in Copley Square and October 18 in Roxbury Cost: Free More information including schedule & locations: website
A huge array 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 to celebrate our local culture of reading and ideas, making the Boston Book Festival the largest literary event in New England.
Featured speakers include Reginald Dwayne Betts, Elizaabeth Strout, Samantha Power, Marie Lu, Erin Etrada Kelly, and Jasmine Guillory - plus many more!
In addition to exhibitions, discussions, sessions for writers, and presentations, you'll find live music, booksellers, food, and kids/teen activities.
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 Cruise 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.
The relaxing 2.5 hour brunch cruise gives you panoramic views of fall colors around the Boston Harbor Islands while you enjoy a tasty 3-course brunch, with mimosas and Bloody Marys available for purchase. You'll see lots of historic sites along the way, and also hear some of the best stories about Harbor Island pirates and ghosts on this narrated cruise.
The 2-hour lunch cruise combines sightseeing and colorful fall foliage around the Boston Harbor Islands and takes you past Long Island Head Light, Boston Light, Fort Warren on Georges Islands, and Fort Independence, as well as numerous islands.
A gourmet picnic lunch and non-alcoholic cold drinks to enjoy on board are included in the price of your ticket, and you can purchase beer, wine, cocktails, and hot beverages. Sit back, relax, and enjoy the gorgeous sights!
Put on your Halloween costume and head over to Boston Common's Frog Pond on Sunday, October 20 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 18 Preview from 4pm-7pm
Oct 19 and 20 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. 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!
Want to enjoy brilliant fall colors right in the city? Boston is filled with trees. Book a room in these hotels, and you'll see these views of stunning autumn color across the street or less than a block away.
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.
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.
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 imagiine, 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:
Northern Lights Cruises:
Brunch Cruise - Savor a delicious 3-course brunch on this relaxing sightseeing cruise around Boston Harbor
Sunday Evening Jazz Cruise - End your weekend on the perfect note by grooving to live jazz as you watch the ever-changing sunset colors as the sun sets behind Boston's city skyline
Winter City Lights Cruise - Unwind on this 1-hour cruise with soothing classical music in the background, perhaps a tasty drink in your hand, and city lights sparking all around you
Winter Sunset Cruise - Grab a cocktail and apps from the bar and then relax as you watch the sun set on this sail around the Harbor, just in time to catch the USS Constitution fire its cannons as the sun dips down past the horizon
Live Irish Music Cruise - Get ready for fun on this rockin' Celtic cruise with a live Irish band playing classic Boston Irish songs, traditional Irish tunes, top hits, and your requests
Galentine's Brunch Cruise - Celebrate friendship by inviting your BFFs on this mouth-watering 3-course brunch cruise for sightseeing around the Harbor, where you may even see porpoises and seals - adult beverages - February 15, 16
Adirondack III Sailing Cruises:
Returns in the spring!
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.
Cape Ann Artisans Open Studios
Don't miss this wonderful excuse to tour artist studios along the beautiful Rockport and Gloucester coast on Columbus Day weekend! 23 artists and artisans at 20 locations 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 12, 13, and 14, 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
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 mid October.
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.
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).
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
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
John Coltrane Memorial Concert
The 42nd Annual John Coltrane Memorial Concert will present an evening of Ballads & Blues, featuring the JCMC Ensemble with Carl Atkins, Phil Grenadier, Bijon Watson, Michael Peipman, Jeff Galindo, Randy Pingrey, George W. Russell Jr, Yoron Israel, Tyler Bonilla, John Lockwood, Bill Lowe, Dorsey Minns, Bill Pierce, Stan Strickland, Bill Thompson, and Bobby Tynes.
The concert takes place on Saturday, October 5 at 7:30 at Northeastern University's Blackman Theatre, 360 Huntington Ave.
Tickets: $25-$40 - tickets & more information here
When: October 30-Nov 1 Where: Hynes Convention Center, 900 Boylston, Back Bay, Boston Closest T station: Green Line / Hynes For more information: 617-369-3204; website Entrance fee: $20 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 130 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.
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 12 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
When: October 9-11
Where: Davis Square, Somerville; Harvard Square, Cambridge 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. 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
Check out all our tips on how to find discounts, deals, and promo codes for Boston hotels. Whether you're looking for bargain accommodations or want to pay less for luxury, we'll show you How to Save on Hotels in Boston.