Boston Discovery Guide's recommendations for the 10 best things to do in Boston in October share a common theme: Soak in the gorgeous October weather, enjoy gold and crimson fall foliage, and join the seasonal celebrations and festivals happening in Boston this month.
Boston's huge Columbus Day Parade, art festivals and open studios, the world-famous Head of the Charles Regatta, interesting walking tours, and New England Patriots football games give you plenty of great excuses to be outside.
And don't forget Halloween events in Boston and nearby Salem all month!
Need more suggestions about what to do in Boston in October? Check the October Events Calendar.
1. Watch Boston's Columbus Day Parade
Marching through Boston's North End neighborhood in odd-numbered years (2019, 2021, 2023) and East Boston during even-numbered years (2018, 2020, 2022), the Columbus Day Parade celebrates the city's Italian heritage, the armed forces and their contributions to American freedom, and implicitly, the voyages and explorations made by Christopher Columbus.
This 2-hour parade attracts more people from the neighborhood than tourists, and chatting with all the neighbors and other groups while watching the bands, military units and honorary militias, floats, performers, clowns, and even antique cars march by adds to the fun.
Be sure to: Go for dinner in one of the mouth-watering North End or East Boston Italian restaurants after the parade:
- North End - You'll find dozens of great choices along and near Hanover and Salem Streets - basically, you'll be happy with whatever you choose if you like Italian cuisine; if not, head to Neptune Oyster (63 Salem St)
- East Boston - Head to Santarpio's Pizza (113 Chelsea St or Belle Isle Seafood (1267 Saratoga St); you'll also find lots of good Central American restaurants along Bennington Street.
2. Celebrate Halloween!
With its many historic graveyards, ghost stories, and grisly murders (think Jack the Ripper), not to speak of millions of pumpkins from the surrounding New England countryside, Boston revels in Halloween, with celebrations and special events going on all month. If you're visiting, not-to-be-missed events are the famous Ghosts and Gravestones tours, ImprovBoston's very funny and totally outrageous GoreFest production, and if you have time, a day trip to Salem, the witch capital of the world.
- More about the Ghosts and Gravestones tour
- More about Halloween events in Boston
- More about Halloween in Salem
Check out half-price (and discount) tickets to Halloween events and shows from Goldstar:
- W Halloween Eve Party @ the W Hotel Boston
- Titanic Masquerade Party Cruise on the Spirit of Boston
- The Woman in Black @ the Davis Square Theatre
- Trick & Treats Halloween Dance Party - Boston Harbor on the Provincetown II
- Rocky Horror Show - Dinner & Theater - Cottage Park Yacht Club, Winthrop
3. Explore Boston by Bike
Another fun thing to do is to join a bike tour led by Urban Aventours (109 Atlantic Ave, just across from Christopher Columbus Park in Boston's North End). Tours depart several times daily, and you can select from a bunch of interesting options, including fall foliage tours.
4. Watch the Head of the Charles Regatta
Sculls (racing boats) powered by rowers ply the Charles River almost year-round - truly a quintessential Boston sight.
But when over 8,000 local and elite rowers from around the world gather for the huge Head of the Charles Regatta in late October, they fill the river with an exciting spectacle that attracts huge crowds along the banks and looking down from the bridges.
Best of all, the Regatta gives you the perfect excuse to be outdoors enjoying fall foliage during the most beautiful season of the year.
Find a great viewing spot from either the Cambridge or Boston side of the river or one of the bridges, and enjoy the races!
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5. Join a Walking Tour
Combine walking around and viewing Boston's fall foliage with seeing interesting parts of the city from an "insider" perspective by taking a walking tour. Here are 4 excellent choices:
- Boston Movie Mile Tour - Fascinating walking tour through Beacon Hill, where you'll see 30+ sites featured in movies and TV shows, and hear the fascinating behind-the-scenes details from the tour guides, all of whom are actors. A 3-hour bus tour option is a great choice for rainy days.
More about the Boston Movie Mile tour and ticket information
- Boston Chocolate Tour - Offered for several neighborhoods including Beacon Hill, Back Bay, the South End, and Cambridge's Harvard Square. Plenty of chances to sample chocolates along the way. Definitely Boston's sweetest tour!
More about the Boston Chocolate Tour and ticket information
- Boston Wine Tasting and Walking Tour - You'll stroll around one of Boston's iconic neighborhoods - the North End, South End, Back Bay, or Harvard Square - while your guide leads you to 3 award-winning restaurants where you'll sip up to 6 different wines while your guide shares information about Boston's culinary scene, wine pairings, and other tips. Boston in October doesn't get much better than this!
Find out more and book your tour now
- Fenway Park Tour - This popular tour takes you right out on the field, up into the Green Monster, and behind the stands at Fenway Park. Lots of fascinating Red Sox lore.
Find out more
More Top Tours for October
6. Indulge in Sports
For Boston sports fans, October offers Bruins, Celtics, and Patriots games. With TD Garden and Fenway Park right in the middle of the city, getting to a game couldn't be easier. Even though Gillette Stadium requires a little more time to reach, you can easily get there and back on the special "Patriot Train" departing from North Station.
7. Visit Open Art Studios
The Fort Point Arts Community, located next to the Fort Point Channel, dividing Downtown Boston from the South Boston Waterfront, has flourished since the first artist pioneers arrived in the 1970s to convert abandoned factories to art studios and galleries. More than 300 artists now live and work there, and on one special weekend in October and another in May, open their studios to the public in one of the city's biggest art events.
Fort Point Open Studios provide a wonderful opportunity to explore the many diverse studios, talk with the artists, and immerse yourself in this world of art. It's also a great excuse to explore more of the rapidly developing South Boston Waterfront.
8. Photograph Boston's Gorgeous Fall Foliage
By early October, Boston's many trees begin to show tinges of gold and crimson and by the end of the month, breathtaking fall foliage can be seen throughout the city.
October is the easiest time of the year to take stunning photos. You'll see plenty of tourists and locals walking around the city with cameras in hand.
If you have to pick just one spot for your foliage viewing/photographing, head to the Lagoon in Boston's Public Garden. With giant weeping willow trees and bright-colored maples of many species reflecting in the water, you can take stunning photos from many different perspectives.
Be sure to check the views from the middle of the suspension bridge - or stand on the shore and make it the focal point of your photos. As an added benefit, Boston's famed swans will still be in residence for most of the month.
Want to combine foliage, sightseeing, and photography? Join a Boston Photography Tour of nearby historic Beacon Hill
9. Enjoy a Concert or Comedy Show
With all the Boston and Cambridge college students back in town, you'll find plenty of entertainment to choose from every night:
Ticket Discount Code: TicketLiquidator - Enter TLSUMMER to get $10 off orders of $250+
Check Boston Discovery Guide's Concert Schedule for October for more ideas.
10. Bask in the Warmth of the Sun
In just another month, October's relatively warm, sunny days will be just a memory - so go outdoors and soak up the sunshine now!
- Patio dining at Boston restaurants - You can still comfortably dine outdoors this month, especially if you're wearing a sweater
- Picnic on the Rose Kennedy Greenway. Need something to eat? Walk over to the Boston Public Market, where you'll find plenty of tasty take-out. More about the Greenway
- Explore a neighborhood - Beacon Hill, across from Boston Common and the Public Garden offers plenty of breathtaking 18th and 19th century architecture.
- Relax on the Esplanade - Boston's Esplanade along the Charles River offers spectacular scenery from wharfs floating just above the water - Find a chair, relax, and enjoy fall foliage along the shore. More about the Esplanade
Return to Top - Things to Do in Boston in October
Join one of the popular 3-hour Whale Watching Cruises departing from the convenient Downtown Boston Waterfront, and you'll have the opportunity to spot whales off the coast of Boston.
You'll see these magnificent creatures close-up from the deck of your ship, and probably spot Humpback and Finback whales and see White Sided Dolphins frolicking in the waters.
Another Option: Get a 3, 5, or 7-day GoBoston Discount Card and choose a free Whale Watching Cruise ticket. Plus, the discount card gives you the free admission to 40+ other top Boston area attractions, for savings totaling up to 55%.