The best Boston events in September 2024

One of the most charming joys of autumn in New England is ditching the city for an orchard to pick your own apples. There are plenty of orchards within a reasonable distance of Boston that welcome folks for pick-your-own apples. For Cortlands, Macouns or whatever variety of apples you like, here's where to go apple picking this fall around Boston.

Steins up! It’s time for Oktoberfest in Boston. Originating way back in 1810, Oktoberfest began as a celebration of the marriage of the crown prince of Bavaria. Since then it's become a large-scale cultural event in Germany that’s centered on beer—and naturally, Boston is all in on any event that revolves around beer. The Hub will see all sorts of Oktoberfest celebrations from mid-September through October. Check out our list of Oktoberfest events (in chronological order) and start making your plans.

Before a new, 300-capacity music venue by the name of Great Scott opens on Harvard Avenue in 2026, the longtime booking agent of the legendary rock club is keeping his chops up at sister bar O'Brien's Pub. Carl Lavin—the original Great Scott’s longtime booking manager—is putting on a seven-night run of shows this month, beginning Sunday, Sept. 22, with Gym Shorts and Dutch Tulips. Tickets for each night of live music range from $12–$15.

Hispanic Heritage Month is celebrated from September 15–October 15. From feasting at one of the best Mexican restaurants in Boston to attending the Noche Latina dance party every Sunday at Time Out Market, there are plenty of easy ways to participate by supporting local businesses. Of particular note: A fundraising crawl is happening in the Seaport through October 15, with $1 from select items at Vela and Deck 12 at YOTEL, Para Maria at the Envoy, Scorpion Bar, Borrachito Taqueria & Spirits and Little Words Project donated to Sociedad Latina. Additionally: Saturday, Sept. 21, and Sunday, Sept. 22, are the final dates to visit the collaborative, traveling beer garden from Boston's first Latin-owned brewery, Roundhead Brewing Co.; and Caribbean American food truck Fresh Food Generation. Catch it on Brighton Common both days.

Whale Song, a new public art installation that pays homage to the majestic sea animals, debuts September 18 outside the New England Aquarium. Crafted by artist Jean-Marie Appriou from molded driftwood and old railroad ties and cast in aluminum, Whale Song represents the historical, mythological and future ways that whales impact our lives. Celebrate the opening of Whale Song—which will be on display in Central Wharf Plaza through August 2025—on Wednesday, Sept. 18, from 4–6pm with the artist and curator.

Before or after, art lovers can also swing by Dewey Square to scope out the new mural by artist Jeffrey Gibson. (See the lead image, above, for a sneak peek!) The colorful work entitled "your spirit whispering in my ear" is officially unveiled on Thursday, Sept. 19, from 6–8 pm with a drag show, art-making activities, food trucks and more.

Nee England's epic answer to the state fair, the Big E is the largest event on the East Coast and the ninth largest in North America. It takes place in West Springfield, Mass. (about two hours from Boston) and represents all the New England states with agricultural exhibits and competitions, rides and amusement park games, musical performances, parades and plenty of fair food. The Big E runs September 13–29. Here's everything you need to know. 

Dinner and drinks deliciously shine at Comfort Kitchen, a 2023 James Beard Best New Restaurant nominee and Time Out Boston's current No. 1 restaurant in the city (ahem!). It recently debuted a new weekends-only brunch with many new dishes and drinks that carry on CK's delicious mission of highlighting ingredients that speak to immigrant experiences. Reservations aren't required yet, like they are at dinnertime, to try new dishes like plantain pancakes with jerk butter, breadfruit hash with nido sauce, and a Bloody Mary made with lemon vodka by Rhodium—a queer female-owned distillery in Rhode Island—yellow tomato, scotch bonnet pepper and Haitian pikliz brine.

Strap into your skates and get roller-disco ready, because Rollerama at Kendall Common is winding down in September. The pop-up roller rink and social space at the corner of Third and Broadway near Kendall/MIT offers free skate rentals Wednesdays–Sundays through September 29. Drinks at the Rink is open with local bartenders serving up the likes of Lamplighter and Remnant Brewing beers, wines curated by Rebel Rebel and more. Concesssions are available for purchase from BUENCIES, a Roller Disco Snack Bar from Buenas and Gracie's Ice Cream; and a rotating selection of food trucks. Programming is on every weekend through September with DJ nights, beginner-friendly skating classes and more. 

COJE Management Group, the Boston-based restaurant group behind Lolita, Ruka, Mariel, Yvonne’s and more splashy spots, unveiled their latest restaurant in September: a moden Chinese bar and lounge called Mr. H. Located at 225 Northern Ave., Mr. H leans into the cuisine of mainland China and Taiwan with the atmosphere of an intimate Shanghainese cocktail lounge. On the menu, "Cold Treasures," "Dumplings and Dim Sum," "Night Market" and "Wok and BBQ" dishes beckon. All plates are designed to be shareable, as well as a treat for eyes. We’re excited to try the crab noodles made with red crab and glass noodles, topped with caviar; and the tangerine tuna, a lightly sweet-and-sour tuna crudo tossed with a spiced, tangerine-infused vinegar. The lights are on nightly from 5pm until late.

While there are plenty of lovely spots across the region to take in the colorful views, you don't need to take a weekend trip to see fall folaige. Leaf peeping in the city is an extra-special way to celebrate the season. Here's where to find the best spots to see Boston’s fall colors for both urban dwellers and city visitors.

For many, the true harbinger of fall is when the lights flicker on for football season at Gillette Stadium. Whether you’re a Patriots fan, follow just for fantasy football, can’t get enough of college ball or all of the above, it’s time to hit the bars for all the fun and festivity of football season. Check out these sports bars and restaurants with big TVs and great atmospheres for watching football in Boston—as well as great beer, drinks and food. Here's where to watch football in Boston.