Boston Discovery Guide's recommendations for the 14 best things to do in Boston in October share a common theme: the joy of being in Boston in the fall.
This is the month to soak up gorgeous October weather, enjoy gold and crimson foliage, and join the seasonal celebrations and festivals happening in Boston this month.
Boston's Indigenous Peoples Day events, 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!
Looking for Fun Things to Do in Boston in October?
- Whale Watching Cruise - Watch whales & other marine life frolic
- Boston Duck Tour & Cruise - See Boston by land & water
- Boston Seafood Tasting Tour - Sample Boston's best seafood on this popular walking tour
- Best of Boston: Private Tour - Explore Boston's history, culture, and food on this popular full-day tour; transportation & pickup included
- History Pub Crawl Tour on the Freedom Trail - Visit Paul Revere's favorite tavern
Check out our roundup of 14 top things to do in Boston in October - everything from top seasonal events to the city's best hidden gems.
Need more suggestions? Check the October Events Calendar.
1. 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 include 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
2. Make One Last Visit to Your Favorite Summer Beer Garden
October is when Boston's seasonal pop-up beer gardens close until their return in the spring.
So plan to stop by for one last enjoyable brew at your favorite beer garden on the Greenway or the Esplanade - or both.
But don't wait - they fold for the season just after Indigenous Peoples Day Weekend, or even earlier if the weather takes a dicey turn. Although they do reappear in May, that's a long time away. So, carpe deum!
3. Explore Boston by Bike
Another fun thing to do in October 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:
Find out more about Boston Bike 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 11,000 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!
Find out more about the Head of the Charles Regatta & Other October Events
Two Easy Ways to Save BIG in Boston
Find out more about Boston discount cards, and how they give you big savings on top attractions.
5. Get Theatre, Concert, or Comedy Show Tickets
Boston locals will tell you that one of the best things to do in October is to catch a performance in Boston's Theatre District, a concert in one of the city's top music venues, or a show in Boston's comedy clubs as the fall entertainment season begins.
Take a look at what's on this month:
Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Boston Theatre District Shows:
Boston theater during October includes touring Broadway hit shows and musicals , kids shows, and comedy:
- Blue Man Group - Charles Playhouse - Multiple shows all month
Find schedule & tickets for all shows
October Concerts in Boston:
Top concerts in Boston for October 2025 include Tate McRae, Bryan Adams, Pat Benatar, and Candlelight Concerts:
- Tate McRae - TD Garden - Oct 17
- Bryan Adams, Pat Benatar, Neil Giraldo - TD Garden - Oct 26
- Candlelight Concerts - Multiple dates in October at various locations
More concerts for October
Boston Comedy Clubs:
Find tickets to all all comedy events in Boston
6. Explore Boston in October on a Food & Beverage 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 three excellent choices:
1. Boston's North End Walking Food Tour - Explore Boston's Italian North End and sample the delicious pizza, pastries, meats, and cheeses that make this neighborhood such a popular destination.
2. Boston Food & Beverage Tours - Sample Boston food and beverage favorites while you tour iconic neighborhoods:
3. Here's a fun rainy-day choice with comfortable bus transport: Guided Craft Brewery Tour with a Snack - Visit famous Boston breweries, cider houses, and distilleries and enjoy samples along with lunch or dinner - plus you get a behind-the-scenes view of how beer is made while you chat with the brewery owners.
7. Indulge Your Passion for Sports
For Boston sports fans, October offers Bruins, Celtics, and Patriots games. With TD Garden 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.
Check out what's on offer, and use this discount code for savings on Bruins, Patriots, and Celtics tickets:
Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Boston Bruins TD Garden Schedule & Tickets for October
Boston Bruins schedule for October
Boston Bruins schedule for all months
New England Patriots Gillette Stadium Schedule & Tickets for October
New England Patriots schedule for all months
Boston Celtics TD Garden Schedule & Tickets for October
Boston Celtics schedule for October
Boston Celtics schedule for all months
8. Admire Boston's Biggest Pumpkins
Boston Public Market, located at 100 Hanover Street near the Rose Kennedy Greenway and City Hall Plaza, showcases locally produced food from 40 or so New England farmers, fishers, and specialty bakers, coffee bean roasters, and candy makers and is always a great place to pick up prepared food for an impromptu picnic or ingredients for dinner at home.
In October, giant pumpkins steal the show. Stop by to admire the biggest and the best - and then browse the booths for a tasty snack.
More Top Tours for October
9. Celebrate Indigenous Peoples Day
Boston celebrates Indigenous Peoples Day on the second Monday of each October, an official federal and state holiday that coincides with the peak of fall foliage season.
If you're visiting this weekend (or local), you can expect an activity-packed 3-day holiday filled with with parades, open artist studios, free admission to some Boston museums, and lots more.
More about Indigenous Peoples Day Events
10. 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.
Get dates and times for the Open Studios from the October Events Calendar
Find out about the Fort Point neighborhood's top chef-owned restaurants
11. 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 - plus get 20-30 professionally-edited digital photography?
Join a Boston Photography Tour of nearby historic Beacon Hill
12. Relax in a "Secret" Boston Garden
Ramler Park in Boston's Fenway neighborhood isn't exactly a secret - after all, you can easily spot it behind a wrought-iron fence as you walk along Peterborough Street located just a stone's throw away from Fenway Park, but not even most locals outside of the neighborhood know that this hidden gem exists.
It's a public park, even though a handful of neighborhood volunteers maintain it, so you can freely walk open the gate, walk in, and claim your spot on one of the blue benches. Or stroll around and smell the heady scents of fall roses.
More about where find to more secret parks in Boston
13. Recommended Day Trip for October: Salem
For a fun and fast day trip from Boston in October, head to Salem - "The Witch City" - where a month-long celebration of haunted happenings, a grand parade, séances, ghouls, ghost stories, witches, pirates, vampires, and the macabre provides lots of fun things to do leading up to Halloween on the 31st.
Getting to Salem from Boston for a day trip or weekend adventure is easy, especially if you hop on the fast ferry from Boston's Long Wharf.
Once you arrive in Salem, stroll around the city's center and check out all the attractions, join a Boos and Brews Haunted Pub Crawl
Find out more about Halloween in Salem
13. 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!
Some suggestions:
- 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
14. Immerse Yourself in Color on Rainy Days
Escape from a day of less-than-perfect October weather by visiting WNDR, Boston's premier digital art experience where immersive, interactive exhibitions will brighten your day.
After you soak up all the colors and sensory experiences at WNDR, continue escaping the weather with a couple of other inside activities. Walk a few blocks to the nearby Charles Playhouse and catch an entertaining show by Blue Man Group, or hop on a Boston trolley sightseeing tour to stay warm while seeing the city's top attractions.
Find out more about WNDR Boston
More to Do in Boston in October
More to See and Do in Boston during October
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