Boston in September: 9 Things to Do Before Everyone Pretends It’s Sweater Weather
Boston shows off in September. Summer patio weather lingers, fall sneaks into the evenings, and festivals, baseball, and outdoor markets give visitors plenty of reasons to enjoy the city outside.
At Boston Crawling, our perfect Boston day naturally includes hidden history, local taverns, and a cold drink. We run an adults-only history tour pub crawl on the Freedom Trail, so of course you’ll find it near the top of this list. We would happily give it all nine spots, but Boston keeps coming up with other good ideas.
Our guides explore downtown Boston with visitors every day, so we know which classic attractions and September events deserve a place in your plans. Whether you visit as a couple, travel with friends, or explore solo, these nine activities will help you make the most of your trip.
1. Enjoy Newbury Street Without the Cars
On September 6, 13, and 20, Open Newbury Street invites pedestrians to take over one of Boston’s most famous shopping streets from 10 a.m. to 6 p.m.
Browse the boutiques, admire the Back Bay architecture, and stop for coffee or a patio drink. Shops and restaurants spill into the road, people-watching becomes an unofficial event, and even Boston’s ongoing parking debate gets the afternoon off.
2. Take the Freedom Trail with Beer
Some people learn best from textbooks. Others learn best while holding a local beer. We created a tour for them.
On the Boston Crawling Independence Pub Crawl, your expert local guide shares Boston’s hidden, hilarious, and occasionally scandalous history. Visit local pubs and historic taverns along the Freedom Trail, hear the stories your social studies teacher left out, discover how beer helped shape Boston and the American Revolution, and meet fellow travelers from around the world.
The crawl works especially well for couples, groups of friends, and solo travelers who like some conversation with their history.
Boston Crawling runs daily crawls at 3:00 p.m. and 7:00 p.m., plus noon crawls on Saturdays and Sundays. The tour lasts 2 hours 15 minutes, welcomes guests ages 21 and older, and starts at the Samuel Adams statue outside Faneuil Hall. Drinks are available for purchase at each stop, so you choose what and how much you drink.
Of course we recommend Boston Crawling. We know the owners, and they seem delightful!
See September availability and book directly with Boston Crawling
3. Catch the Boston Arts Festival on the Waterfront
The Boston Arts Festival brings Boston-area artists and musicians to Christopher Columbus Waterfront Park on September 12 and 13. The free festival runs throughout both days.
Browse locally made art while live music plays beside the harbor, then walk to the North End, Faneuil Hall, or Boston Public Market. Art, history, Italian food, and drinks within walking distance – Boston occasionally makes vacation planning suspiciously easy.
4. Arrive Hungry at the Boston Local Food Festival
On September 20, the Boston Local Food Festival fills the Rose Kennedy Greenway with local farms, restaurants, chefs, food producers, demonstrations, and live entertainment.
Come hungry. Pants with a forgiving waistband would also demonstrate excellent advance planning. After you finish “sampling,” continue to the North End, Boston Public Market, Faneuil Hall, or an afternoon pub crawl.
5. Experience a Red Sox Game at Fenway Park
The Red Sox play several home games at Fenway Park during the first half of the month. Check the official Red Sox schedule for opponents, times, and tickets.
Fenway combines more than a century of history with famous quirks, passionate fans, and the Green Monster. Grab something to eat, sing with thousands of strangers, and develop a surprisingly strong opinion about a relief pitcher you discovered three hours earlier.
6. Browse the SoWa Open Market
Every Sunday from 11 a.m. to 5 p.m., the SoWa Open Market brings local artists, farmers, food trucks, live music, and brewery takeovers to Boston’s South End. The 2026 season runs through November 15, and admission is free.
Browse the market, grab lunch from a food truck, sip a local beer, and explore nearby galleries and shops. Admission costs nothing, although the vendors make leaving empty-handed impressively difficult.
7. Take a Ferry to Spectacle Island
September offers one of the final chances of the season to explore the Boston Harbor Islands by ferry. Hike, visit historic sites, enjoy a beach, or take in Boston’s skyline from a completely different angle.
Daily summer ferry service ends after September 7, and a more limited fall schedule begins September 10. Check the schedule before choosing your island, and bring water, comfortable shoes, a light layer, and snacks for the ride.
8. Walk Through Beacon Hill and the Public Garden
Start in the Public Garden, cross Boston Common, and wander toward Beacon Hill and Charles Street. Brick sidewalks, gas lamps, historic homes, local shops, and picture-perfect streets reward anyone who enjoys exploring on foot.
September supplies warm afternoons, cooler evenings, and the first touches of seasonal color. One local language lesson: Bostonians call it Boston Common, never “the Commons.” Master that, and you have completed more homework than our pub crawl requires.
9. Finish the Day in the North End
End your day with Italian food and dessert in Boston’s North End. The neighborhood packs restaurants, cafés, bakeries, and enough competing cannoli opinions into a few blocks to inspire years of delicious research.
Reserve a dinner table for a busy weekend, save room for something sweet, and finish with a waterfront walk. Dessert plus light cardiovascular activity equals balance.
Make the Most of Boston This September
In September, Boston serves up warm afternoons, lively neighborhoods, festivals, markets, baseball, history, food, and harbor adventures. Choose a neighborhood, catch an event, eat something local, and leave room for spontaneity.
If you prefer your Boston history with entertaining guides, local taverns, cold drinks, and a drink menu in place of a final exam, come crawl through history with us.
Book the Independence Pub Crawl directly with Boston Crawling