Looking for the best things to do in Boston in September? You're visiting during one of the best months to explore the city.
September brings comfortable weather, fewer summer crowds, fall events, concerts, sporting events, food festivals, and plenty of opportunities to explore Boston's historic neighborhoods. It's also a great time to enjoy outdoor activities before colder weather arrives.
As local Boston tour guides, we've put together this guide to the best things to do in Boston in September, including top attractions, September events, free activities, things to do at night, and family-friendly activities.
If you're planning a trip at another time of year, check out our complete guide to things to do in Boston for even more ideas.
- Top 10 Things to Do in September
- Things to Do at Night
- Free Things to Do
- Family-Friendly Activities
- Boston Weather in September
- Boston Walking Tours
If you're planning a trip at another time of year, check out our complete guide to things to do in Boston for even more ideas.
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Top 10 Things to Do in Boston in September
September is a busy month in Boston, with something happening almost every weekend. Here are 10 of our favorite things to do, from exploring historic sites to attending concerts and festivals.
1. Attend a Concert or Music Festival
Boston has a busy music scene, and September is a great month to see a major concert, catch a smaller performance, or enjoy an outdoor music event.
Major artists regularly perform at venues throughout Boston and the surrounding area, including TD Garden, Fenway Park, MGM Music Hall at Fenway, and other local venues.
September's concert calendar changes every year, so check current listings for performances during your visit.
You can also look for local music festivals and outdoor concerts taking place throughout the Boston area.
2. See a Major Sporting Event
September is an exciting time for sports fans in Boston.
The Boston Red Sox are in the final stretch of the regular season, making a trip to Fenway Park a quintessential Boston experience. Football season also gets underway, with the New England Patriots returning to the field.
Soccer fans can look for matches featuring the New England Revolution, while college sports return to campuses throughout the area.
Even if you don't have tickets to a game, you can still experience Boston's sports culture by visiting Fenway Park and exploring the surrounding Fenway neighborhood.
Want to see inside the legendary ballpark? Check out our guide to Fenway Park tours.
3. See a Live Comedy Show
Boston has a lively comedy scene, with stand-up performances taking place throughout the city and surrounding area.
September's schedule typically includes nationally touring comedians as well as local comedy shows. Popular venues include Laugh Boston, the Wilbur Theatre, City Winery, and other comedy clubs around the city.
Because comedy schedules change from year to year, check the current listings for shows taking place during your visit.
See comedy shows in Boston and find tickets for performances during your stay.
Comedy Clubs
City Winery Bostonoston has a long history of producing comedians, and there are plenty of opportunities to see live comedy in September.
Look for performances by nationally known comedians as well as local stand-up shows.
Some Boston-area comedy venues include:
Check their current schedules for performances during your visit.
Looking for something to do after dark? A comedy show is an easy way to spend a September evening in Boston.
4. Take a Walking Tour
September's comfortable weather makes it an excellent month to explore Boston on foot.
Boston's compact historic center is filled with landmarks, historic streets, parks, churches, and neighborhoods that are best experienced at walking pace.
Tours by Foot offers guided walking tours that explore some of Boston's most fascinating neighborhoods and historic sites.
The Freedom Trail is an obvious choice for first-time visitors, but don't stop there. Boston's neighborhoods have stories that go far beyond the famous red brick trail.
You can also explore areas such as Beacon Hill, the North End, Back Bay, and the Boston waterfront.
Explore Boston walking tours and find a tour that fits your visit.
If you prefer exploring independently, our Boston audio tours let you discover the city at your own pace.
5. Attend a Boston Food Festival
September is a great month for food lovers in Boston.
The city hosts food festivals and special culinary events throughout the month, giving visitors the opportunity to sample everything from local specialties to international cuisine.
One event to look for is the Boston Local Food Festival, which celebrates local farmers, restaurants, food trucks, and sustainable food.
The festival traditionally takes place along the Rose Kennedy Greenway and includes food vendors, demonstrations, live entertainment, and activities for families.
Check the official event information for the current year's date and schedule.
And if you want to eat your way through one of Boston's most historic neighborhoods, consider joining a Boston food tour.
6. Visit the New England Aquarium
The New England Aquarium is one of Boston's most popular attractions and a particularly good choice for families.
Located on Boston's waterfront, the aquarium is home to thousands of marine animals, including sea turtles, penguins, sea lions, and the enormous ocean tank.
One feature you can enjoy without purchasing an aquarium ticket is the outdoor harbor seal exhibit. The seals are located on the plaza outside the aquarium, making them an easy stop while exploring the waterfront.
If you plan to visit the aquarium, check current hours and ticket information before you go.
7. Attend the Boston Arts Festival
September is a great time to experience Boston's local arts scene.
The Boston Arts Festival brings artists and musicians together for a weekend of art, music, and entertainment along the waterfront.
You'll find artists displaying paintings, photography, jewelry, sculpture, and other works, along with live performances.
The festival takes place at Christopher Columbus Waterfront Park and is a fun way to experience Boston's creative community while enjoying the waterfront.
Check the festival's official website for the current dates and schedule.
8. Explore Boston's Top Attractions
There's much more to Boston than the Freedom Trail.
History lovers can visit the USS Constitution, Bunker Hill Monument, Old State House, and Faneuil Hall Marketplace.
You can also visit the Boston Public Garden, Boston Common, Beacon Hill, the North End, and the waterfront.
Fans of the classic television show can stop by the famous Cheers Bar, while visitors interested in history can explore some of Boston's many museums and historic sites.
For more ideas, see our complete guide to Boston's top tourist attractions.
9. Attend the Festival of San Gennaro
The Festival of San Gennaro takes place in Boston's historic North End each September. This lively Italian-American celebration features food, live entertainment, and a festive atmosphere throughout the neighborhood.
It's a great time to explore the North End, one of Boston's most historic neighborhoods, while enjoying its restaurants, bakeries, and historic sites.
Check the Festival of San Gennaro Boston Facebook page for this year's dates, schedule, and event details.
10. Save Money with a Boston Attraction Pass
If you plan to visit several major Boston attractions, a tourist attraction pass may help you save money.
Depending on the pass you choose, you may find admission or discounts for attractions and activities such as:
- New England Aquarium
- Boston sightseeing tours
- Museums
- Historic attractions
- Harbor cruises
- Boston Children's Museum
Before purchasing a pass, make a list of the attractions you want to visit and compare the individual admission prices with the cost of the pass.
For a detailed comparison, see our guide to Boston tourist attraction discount passes.
Things to Do in Boston at Night in September
September evenings can be cooler than summer nights, but Boston remains lively after dark.
From harbor cruises and historic neighborhoods to comedy shows and evening tours, there are plenty of ways to experience the city after sunset.
For more ideas, check out our complete guide to things to do at night in Boston.
Take a Sunset or Evening Cruise
September can be an excellent time for a cruise around Boston Harbor.
As the sun goes down earlier, you'll have a chance to watch the city skyline light up while enjoying the cooler evening air.
Depending on the schedule, you can choose from sightseeing cruises, sunset cruises, dinner cruises, and other harbor excursions.
See our guide to Boston boat tours for options.
See the Boston Skyline
Boston has several places where you can enjoy views of the city skyline.
For a historic perspective, visit Bunker Hill Monument in Charlestown. The monument rises 221 feet above the surrounding neighborhood and offers impressive views when the observation area is open.
You can also head across the harbor to East Boston for views of downtown Boston from the waterfront.
Piers Park is one option for seeing the skyline from across the water.
Take an Evening Walking Tour
Boston's history doesn't disappear when the sun goes down.
An evening tour can offer a completely different perspective on the city's historic neighborhoods.
Tours by Foot offers several private guided experiences that can be particularly interesting after dark, including our Beacon Hill Crime Tour and Boston Ghost Tour.
You can also explore the Freedom Trail independently in the evening, although some historic sites will be closed after regular business hours.
Free Things to Do in Boston in September
Boston doesn't have to be an expensive city to visit.
There are plenty of free things to do in September, from exploring historic neighborhoods and public parks to attending free concerts and seeing some of the city's landmarks.
For even more ideas, check out our complete guide to free things to do in Boston.
Enjoy Free Live Music
Boston has a strong music scene, and free outdoor concerts are often scheduled during the warmer months.
Berklee College of Music's Summer in the City series has traditionally featured hundreds of free performances throughout the Boston area during the summer season.
The September schedule varies from year to year, so check the current Berklee calendar before planning your visit.
See the Harbor Seals at the New England Aquarium
You don't need to purchase admission to the New England Aquarium to see its harbor seals.
The seals are located in an outdoor exhibit on the plaza in front of the aquarium, so you can stop by and watch them without entering the aquarium.
This is an easy free activity to add to a day exploring Boston's waterfront, especially if you're traveling with children.
If you do decide to visit the aquarium afterward, you can purchase New England Aquarium tickets here. Admission may also be available at a discount through some Boston tourist attraction passes.
Visit Bunker Hill Monument
History buffs can visit the grounds of Bunker Hill Monument for free.
The 221-foot monument commemorates the Battle of Bunker Hill, one of the first major battles of the American Revolution.
When the monument's observation deck is open, visitors can climb the stairs for panoramic views of Boston. Access to the top may require a free timed pass, so check with the National Park Service for current information.
Explore Boston's Public Parks
Boston is home to some beautiful public parks that are completely free to visit.
Walk through Boston Common and the Public Garden, admire the famous Swan Boats, or stroll along the Charles River Esplanade.
September's comfortable weather makes it an ideal time to explore these outdoor spaces.
Explore Boston's Historic Neighborhoods
One of the best free things to do in Boston is simply walk.
Explore Beacon Hill's historic streets, wander through the North End, visit the waterfront, or follow portions of the Freedom Trail.
Boston's historic center is compact enough that you can see several major landmarks in a single walk.
Family-Friendly Things to Do in Boston in September
Boston is a great destination for families, and September offers plenty of activities for children and adults.
For more ideas, see our complete guide to things to do with kids in Boston.
Visit Faneuil Hall Marketplace
Faneuil Hall Marketplace is a fun stop for families visiting downtown Boston.
The marketplace is filled with shops, restaurants, food vendors, and outdoor entertainment. Street performers have been entertaining visitors here for decades.
It's also conveniently located near several major Boston attractions, making it easy to combine with a day of sightseeing.
See our guide to Faneuil Hall Marketplace for more information.
Visit the New England Aquarium
The New England Aquarium is one of the easiest family-friendly attractions to add to a Boston itinerary.
Children can see penguins, sea turtles, seals, and thousands of other marine animals while exploring the aquarium's exhibits.
The waterfront location also makes it easy to combine an aquarium visit with a harbor cruise or walk along the Rose Kennedy Greenway.
Ride the Swan Boats
If you're visiting Boston at the beginning of September, check the Swan Boats' operating schedule.
The iconic boats have operated in the Boston Public Garden for generations and provide a short, relaxing ride through the lagoon.
Because the operating season ends in early September, visitors should check the current schedule before making plans.
Look for Boston's Family Festivals
September brings several family-friendly festivals and special events to Boston and the surrounding area.
Depending on the year, you may find outdoor festivals featuring music, food, art, crafts, and activities for children.
Check local event calendars for events taking place during your specific dates.
Visit the Tortoise and Hare Statues
If you're exploring the Back Bay, look for Boston's bronze Tortoise and Hare statues near Copley Square.
The statues are inspired by the famous fable and make a fun photo stop for families.
They're also located close to the Boston Marathon finish line, Trinity Church, and the Boston Public Library, making it easy to include them during a Back Bay sightseeing walk.
Attend Boston Lights
Boston Lights: A Lantern Experience returns to Franklin Park Zoo from August 14 through November 8, 2026, making it a great evening activity if you're visiting Boston in September.
The 72-acre zoo is transformed after dark with colorful, larger-than-life lantern displays inspired by wildlife, nature, and cultures from around the world. The 2026 experience includes illuminated scenes featuring animals, ocean life, plants, and other spectacular displays.
From August 14 through September 30, Boston Lights is open Thursday through Monday from 6:00 pm to 10:30 pm. Tickets are required, and advance reservations are recommended because evenings can sell out.
Visit the Boston Lights website for tickets, current hours, and additional information.
More September Events Around Boston
If you're staying in Boston for several days, you may also want to look beyond the city center.
Some major September events take place within driving distance of Boston, including festivals, fairs, concerts, and seasonal attractions.
Events and dates change each year, so check the official event websites before making plans.
The Big E
The Big E in Springfield, Massachusetts, is one of New England's largest annual fairs.
The event features rides, food, live entertainment, agricultural exhibits, competitions, and much more.
It's a long way from downtown Boston, so consider the travel time before adding it to a short Boston itinerary.
Jack-O'-Lantern Spectacular
For a preview of Halloween, the Jack-O'-Lantern Spectacular at Roger Williams Park Zoo in Providence features thousands of illuminated pumpkins.
The event typically begins in September and continues into November.
It's an evening event, making it a fun option for families looking for something different to do after dark.
What Is the Weather Like in Boston in September?
September is one of the most comfortable months to visit Boston.
Early September can still feel like summer, while temperatures generally become cooler as the month progresses. You can expect a mix of warm days, cooler evenings, and occasional rain.
Because you'll likely spend a lot of time walking, comfortable shoes and layers are a good idea.
For average temperatures, precipitation, what to pack, and a more detailed forecast, see our complete guide to Boston weather in September.
Explore Boston with Tours by Foot
September is an excellent month to explore Boston on foot.
From the Freedom Trail and historic Beacon Hill to the North End and Boston's waterfront, there's a lot to discover beyond the city's most famous landmarks.
Tours by Foot offers guided walking tours that bring Boston's history, neighborhoods, food, and stories to life.
Explore our Boston walking tours and find an experience that fits your trip.
Related Boston Guides
- Boston Weather in September
- Free Things to Do in Boston
- Things to Do with Kids in Boston
- Boston's Free Museums
- Luggage Storage in Boston
- Freedom Trail Tours
- Boston Tourist Attractions
