October is one of the best times of year to visit Boston. Fall foliage, crisp weather, historic neighborhoods, and a full calendar of events make the city especially fun to explore.
Take a walk along the Freedom Trail, admire the fall colors in Boston Common and the Public Garden, explore Beacon Hill, or head across the Charles River to Cambridge. October also brings major annual events, including the Head of the Charles Regatta, the Boston Book Festival, Oktoberfest celebrations, and Halloween events.
Whether you're visiting Boston for a weekend or spending several days exploring New England, you'll find plenty of things to do in Boston in October.
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- Top 10
- Free Things to Do
- Things to Do at Night
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- Weather
- Things to Do (any time of year)
TOP 10 THINGS TO DO IN BOSTON IN OCTOBER
Boston is especially beautiful in October, when fall foliage, cooler temperatures, historic sites, and seasonal events make the city fun to explore.
From walking the Freedom Trail and watching the Head of the Charles Regatta to seeing fall colors, visiting historic cemeteries, and celebrating Halloween, there are plenty of things to do in Boston in October.
Here are 10 of our favorite things to do in Boston during October.
If you're looking for even more ways to explore the city, check out our guides to:
It’s also worth noting that you can save money on some of the most entertaining attractions in and around the city with a Boston tourist pass.
1. Walk the Freedom Trail
October is an excellent month to explore Boston's historic sites on foot.
The Freedom Trail connects some of the city's most important Revolutionary-era landmarks, including Boston Common, the Old State House, the Boston Massacre Site, Faneuil Hall, Paul Revere's House, and the Bunker Hill Monument.
The cooler October weather can make a long walking tour much more comfortable than during the heat and humidity of summer.
Our Boston Freedom Trail walking tour visits many of the most important sites along the trail. You can pay what you wish or prepay when booking your tour.
If you'd prefer to explore independently, you can also take our Boston Freedom Trail audio tour, which lets you learn about the historic sites at your own pace.
2. See the Fall Foliage
October is one of the best months to experience fall colors in Boston.
You can find changing leaves throughout the city's parks, historic neighborhoods, and along the Charles River. Boston Common, the Public Garden, and the Charles River Esplanade are all easy places to enjoy the autumn scenery without leaving the city.
Peak foliage varies from year to year and generally arrives earlier farther north and later around Boston. If you have extra time, you can also take a day trip outside the city to see more dramatic New England foliage.
If you're looking for a longer fall outing, consider combining a foliage drive with a visit to one of the area's apple orchards or farms.
See our guide to fall foliage and apple picking around Boston for more ideas.
3. Watch the Head of the Charles Regatta
The Head of the Charles Regatta is one of Boston's biggest annual October events and a great way to experience the city during the fall.
Thousands of rowers compete along the Charles River, while spectators gather along the riverbanks to watch the races and enjoy the festival atmosphere.
The 2026 Head of the Charles Regatta takes place October 16–18.
Watching the races from along the Charles River is free, although some viewing areas and event experiences require admission.
If you'd rather get out on the water yourself, you can also look into Boston boat cruises.
4. See a Show or Comedy Performance
Boston has plenty of live entertainment in October, from Broadway and theater productions to stand-up comedy.
For comedy, Laugh Boston has comedians performing throughout the month, including:
- October 1: The Kenny VS Spenny 2026 USA Comedy Tour
- October 9–10: Amber Autry
- October 16–17: Robert Kelly
- October 23–24: Ryan Davis
- October 29: Jessimae Peluso
Shows
Some shows scheduled for October 2026 include:
- Monty Python's Spamalot — October 6–11 at the Wang Theatre
- Outlander in Concert — October 10 at the Shubert Theatre
- Coco in Concert Live to Film — October 30–31 at Symphony Hall
You can also check Boston's theater and Broadway schedules for performances during your visit. Dates and performances can change, so check current listings before you go.
5. Celebrate Oktoberfest
October is a great time to enjoy Oktoberfest celebrations in Boston and the surrounding area.
You'll find seasonal events featuring German food, beer, live music, dancing, and other fall activities at venues throughout Greater Boston. Harvard Square has traditionally hosted Oktoberfest celebrations, while breweries, restaurants, and other local venues may also offer their own events.
Dates, locations, and activities vary from year to year, so check current event listings before you go.
If you're visiting Boston in October, Oktoberfest is an easy way to combine the city's fall atmosphere with a lively seasonal celebration.
6. Explore Boston's Historic Graveyards
With Halloween approaching, October is a great time to explore some of Boston's historic burying grounds.
The Granary Burying Ground is one of the city's best-known historic cemeteries. Located along the Freedom Trail, it is the final resting place of several prominent figures from the American Revolution, including Paul Revere and three signers of the Declaration of Independence.
You can also visit Copp's Hill Burying Ground, which dates to the 17th century and is one of Boston's oldest burial grounds.
Both cemeteries are located near other major historic attractions, making them easy to include while exploring Boston on foot.
They are also included on our Boston Freedom Trail walking tour, where you can pay what you wish or prepay, or you can explore the sites independently with our Boston Freedom Trail audio tour.
7. Take a Day Trip to Salem
October is one of the busiest and most popular times of year to visit Salem, Massachusetts.
The city is closely associated with the 1692 Salem Witch Trials, and Halloween-season events bring visitors throughout the month. You can visit the Salem Witch Museum, explore historic sites, take a walking tour, or simply spend the day exploring the city's historic streets.
If you're traveling from Boston, the MBTA ferry from Long Wharf to Salem is a scenic way to make the trip. Allow plenty of extra time for transportation and crowds, particularly on weekends in October.
See our guide to taking the ferry from Boston to Salem for information about the route, schedules, and what to expect.
8. See a Concert or Show
Boston has a packed concert calendar in October, with everything from major touring artists to classical performances.
Some concerts scheduled for October 2026 include:
- Gorillaz — October 1 at TD Garden
- The Smashing Pumpkins — October 2 at TD Garden
- Olivia Rodrigo — October 15, 17 & 18 at TD Garden
- Steve Lacy — October 13 at MGM Music Hall at Fenway
- Sin Bandera — October 17 at the Wang Theatre
For classical music, the Boston Symphony Orchestra also performs throughout October at Symphony Hall, including programs featuring Beethoven and Tchaikovsky.
Check current concert schedules for additional performances and ticket information.roughout October, including a world premiere by Tod Machover on October 22–24.
You can also take a free tour of Symphony Hall during the Boston Symphony season. See our guide to free tours of Symphony Hall for more information.
9. Catch a Boston Sports Game
October is a great time to catch a professional sports game in Boston. Depending on your visit, you can see the Patriots, Bruins, Celtics, or professional soccer.
Some October home games include:
- Patriots: October 11 vs. Las Vegas Raiders; October 18 vs. New York Jets
- Bruins: October 5 vs. Ottawa Senators; October 31 vs. Chicago Blackhawks
- Celtics: October 23 vs. New York Knicks; October 26 vs. Chicago Bulls
- New England Revolution: October 10 vs. Seattle Sounders; October 17 vs. Chicago Fire
Check the teams' schedules for additional games, times, and tickets.
Not visiting during a game? You can also take a Fenway Park tour and explore the historic home of the Boston Red Sox.
10. Celebrate Halloween in Boston
October brings plenty of Halloween fun to Boston, from family-friendly events and seasonal activities to parties and evening celebrations.
You can explore Boston's historic neighborhoods, visit historic cemeteries, or look for Halloween events taking place around the city.
Check local event calendars for activities and celebrations happening during your visit.
Free Things to Do in Boston in October
You don't have to spend a lot of money to enjoy Boston in October. From historic sites and free festivals to fall foliage and outdoor activities, there are plenty of ways to experience the city on a budget.
For even more ideas, check out our guide to free things to do in Boston.
Visit a Free Museum
Boston has several museums and historic sites that offer free admission, either every day or during special programs.
For something a little unusual, you can visit medical-history collections such as the Ether Dome, Russell Museum, or Warren Anatomical Museum. Some exhibits contain medical specimens and historical material that may not be suitable for everyone.
You can also find free or discounted admission at some of Boston's art and history museums on specific days.
For more ideas, see our guide to free museums in Boston.
Attend Harvard Square's Oktoberfest
Harvard Square's Oktoberfest is one of the area's biggest free fall celebrations.
The 47th Annual Harvard Square Oktoberfest takes place October 11, 2026, with a rain date of October 12. The event traditionally features live music, food, crafts, family-friendly activities, and the annual HONK! Parade.
Check the Harvard Square event schedule for the latest information before you go.
Find Something to Read at the Boston Book Festival
The Boston Book Festival returns to Copley Square on Saturday, October 17, 2026.
The free festival brings authors, readers, and families together for author talks, workshops, panels, exhibitors, and other literary events. The 2026 festival is scheduled for 10 a.m. to 6 p.m. in Copley Square.
Learn more about the Boston Book Festival.
TIP: Even if you miss the festival, the historic Boston Public Library in Copley Square is worth visiting. You can explore the building, see its historic architecture, and check its calendar for free programs and tours.
Visit the U.S.S. Constitution & Bunker Hill Monument
Two of Boston's most important historic attractions are also free to visit.
The U.S.S. Constitution, better known as "Old Ironsides," is the world's oldest commissioned warship afloat. Admission aboard the ship is free, although visitors age 18 and older may need to show a valid photo ID at the security entrance.
Across the river in Charlestown, the Bunker Hill Monument and Bunker Hill Museum are also free. You can visit the museum and, when the monument is open for climbing, climb the 294 steps to the top for views over Boston.
Both locations are part of the Freedom Trail and can be visited while exploring Boston's historic sites.
They are also included on our Boston Freedom Trail walking tour, where you can pay what you wish or prepay when booking.
If you'd rather explore independently, our Boston Freedom Trail audio tour lets you learn about the historic sites at your own pace.
Things to Do at Night in Boston in October
Boston has plenty to do after dark in October, from spooky experiences and stargazing to live entertainment and evening walks.
For even more ideas, see our guide to things to do at night in Boston.
Take a Haunted Tour
October is a great time to explore Boston after dark on a haunted tour.
Boston's historic streets, old cemeteries, and centuries of history provide plenty of material for ghost stories and tales of the city's darker past. A haunted bus tour is also a good option if you'd rather see more of Boston while staying out of the cold.
Go Stargazing at the Boston University Observatory
If you happen to visit Boston on a clear evening, consider spending the night looking at the stars.
The Boston University Observatory regularly hosts public observing nights at Coit Observatory, where visitors can learn about astronomy and, when weather permits, look through telescopes at objects in the night sky.
The program is free, but advance registration is required and observing nights can fill up quickly. Programs may also be canceled or changed because of weather.
Check the Boston University Observatory schedule before visiting.
See a Show or Concert
October is a great time to catch live entertainment in Boston after dark.
You can see Broadway productions, theater performances, comedy shows, and concerts at venues throughout the city. Check current schedules to find performances taking place during your visit.
You can also see our sections above for specific October shows and concerts in Boston.
Family-Friendly Activities in October
October is a great time for families to visit Boston. You'll find fall foliage, seasonal festivals, Halloween activities, museums, and attractions that kids and adults can enjoy together.
For even more ideas, see our guide to things to do with kids in Boston.
Visit Boston Lights
Boston Lights at Franklin Park Zoo is a popular evening activity for families in October.
The event features illuminated displays throughout the zoo, creating a fun way to experience the zoo after dark. Check the current schedule and ticket information before visiting.
Take a Look at the Fall Foliage
October is one of the best times of year to see fall colors around Boston.
You can enjoy the changing leaves in parks and along the Charles River, or head outside the city for more extensive foliage. Families can combine a fall outing with a visit to an orchard or farm for apple picking, cider, and other seasonal activities.
See our guide to fall foliage and apple picking around Boston for ideas.
Go Apple Picking
If you have a car and want to get outside Boston, October is a great time to go apple picking.
Several orchards and farms in the area offer apple picking along with seasonal favorites such as fresh apple cider, cider donuts, hayrides, farm animals, and pumpkin patches. Availability varies throughout the season, so check each farm's current picking schedule before you go.
Apple picking also makes a great family day trip and can easily be combined with a drive to see the fall foliage.
See our guide to fall foliage and apple picking around Boston for more ideas.
Learn All About the Salem Witch Trials
October is a popular time to visit Salem, Massachusetts, especially for travelers interested in the history of the Salem Witch Trials and the city's Halloween traditions.
The Salem Witch Trials of 1692 are an important part of the city's history. Visitors can learn more about the trials at the Salem Witch Museum and explore historic sites throughout Salem.
If you're traveling from Boston, the MBTA ferry from Long Wharf to Salem is a scenic way to make the trip. October weekends can be especially busy, so allow extra time for transportation and crowds.
See our guide to taking the ferry from Boston to Salem for information about the route and what to expect.
For more ideas, see our section above about taking a day trip to Salem.
Take the Kids to a Corn Maze or Pumpkin Patch
For a classic fall activity, take the kids to a corn maze or pumpkin patch at one of the farms outside Boston.
Many farms offer more than just pumpkins and corn mazes, with activities such as hayrides, farm animals, seasonal food, and other fall attractions. Some also offer nighttime or haunted activities for older children.
Connors Farm in Danvers is one option to consider. Its fall attractions typically include a themed corn maze and other seasonal activities.
Check the farm's current schedule before visiting, since attractions, hours, and admission prices can change from year to year.
TIP: You can easily combine a visit to a farm with a fall foliage drive or apple-picking trip. Some farms are also within easy reach of Salem, making it possible to combine several October activities in one day.
Visit the New England Aquarium
Enjoy a day under the sea at the New England Aquarium, one of Boston's most popular family attractions.
You can see penguins, seals, sea turtles, and thousands of other marine animals, including Myrtle, the aquarium's famous green sea turtle. The aquarium's central ocean tank is also a highlight, with multiple levels offering views of the marine life.
The aquarium is located on Boston's waterfront, making it easy to combine with a walk along the Harborwalk or other downtown attractions.
Admission is charged, so check the New England Aquarium website for current ticket prices, hours, and special programs before your visit.
TIP: This is also a good option for a rainy or chilly October day when you want to spend a few hours indoors.
Eat at Faneuil Hall Marketplace
Faneuil Hall Marketplace is a convenient place to stop for lunch, dinner, or a snack while exploring downtown Boston.
The marketplace has plenty of food options, including New England favorites such as lobster rolls and clam chowder, along with pizza, sandwiches, and other casual choices. You can also browse the shops and watch the street performers and musicians who regularly entertain visitors.
Faneuil Hall Marketplace is located near several major Boston attractions, making it easy to include during a day of sightseeing.
Check the Faneuil Hall Marketplace event calendar for seasonal events and activities taking place during your visit.
You can also learn more about the history and attractions of Faneuil Hall Marketplace.
Halloween in Boston
Boston is a fun place to visit around Halloween, with family-friendly festivals, spooky attractions, haunted tours, and Halloween parties taking place throughout October.
Fall-o-Ween Children's Festival
Families can celebrate Halloween at the Fall-o-Ween Children's Festival at the Boston Common Frog Pond on October 16, 2026.
The free event includes Halloween activities, costumes, music, arts and crafts, a trackless train, games, and a haunted zombie maze. The festival runs from 5–8 p.m. and is designed for children and families.
PruBoo at Prudential Center
PruBoo returns to the Prudential Center on October 25, 2026, from 11 a.m. to 1 p.m.
The free family event includes trick-or-treating at participating stores and restaurants, face painting, magic shows, Halloween crafts, and live music.
Take a Haunted Tour
If you'd rather experience Boston's spooky side, October is a great time to take a haunted tour after dark. Boston's historic streets, burying grounds, and centuries of history provide plenty of material for ghost stories and tales of the city's darker past.
Take Part in a Spooky Bar Crawl
If you're 21 or older and want to celebrate Halloween after dark, a Boston bar crawl is one way to spend the evening in costume while exploring some of the city's nightlife.
Several Halloween bar crawls are scheduled for October 2026, including events in Faneuil Hall and Fenway. The Boston Official Halloween Bar Crawl is scheduled for October 30 and 31, while the Boston Fenway Official Halloween Bar Crawl takes place October 31.
Another option is the Trick or Drink Halloween Bar Crawl, which has events scheduled for October 24, 30, and 31.
These are ticketed, 21+ events, and details such as participating bars and check-in locations can change, so check the event information before making plans.
Celebrate Halloween Night
On October 31, you'll find Halloween parties, themed events, cruises, live entertainment, and other celebrations around Boston. Events range from family-friendly activities to adults-only Halloween parties, so check age requirements and event details before making plans.
For more Halloween events and current listings, check Boston's official Halloween guide.
Boston Weather in October
October is one of the most pleasant months to visit Boston, with cooler temperatures, fall foliage, and generally comfortable conditions for exploring the city on foot.
Average daytime temperatures are typically in the 60s°F, while evenings can be noticeably cooler. Since temperatures can change throughout the day, dressing in layers is a good idea.
October can also bring rain, so pack a waterproof jacket or umbrella along with comfortable shoes for walking.
For more information, see our guide to Boston weather in October, including average temperatures, rainfall, and what to pack.
Consider a Boston Tourist Pass
If you're planning to visit several paid attractions during your trip, a Boston tourist pass may help you save money compared with buying individual tickets.
Depending on the pass, you may get admission to attractions such as museums, historic sites, cruises, and other popular Boston activities.
Before purchasing a pass, compare the included attractions with your itinerary to make sure you'll visit enough attractions to make it worthwhile.
See our guide to Boston tourist passes for a comparison of the available options.
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