As the crisp air settles in and the leaves transition to familiar hues of reds, oranges, and yellows, it’s undeniable that fall has arrived in Boston. Here at The Envoy Hotel, Autograph Collection, we’re excited to guide you through the city’s best activities that will help you embrace the spirit of the season.

Raise a Toast to Oktoberfest in Boston

Celebrate Oktoberfest in Boston with a twist. Contrary to the name, most of these lively events take place in late September, spilling the fun into fall. Boston’s burgeoning craft brewery scene means you’ll find different Oktoberfest events scattered throughout the city. Sip on specialty German beer or local brews, snack on bratwurst and pretzels, and listen to live music.

Attend the Head of the Charles Regatta

In late October, the Charles River transforms into a bustling stage for rowers from around the globe during the iconic Head of the Charles Regatta. As the river glimmers with racing boats and the city is saturated with the rich colors of fall foliage, take the opportunity to witness this one-of-a-kind event. Whether you choose to watch from a bridge or the riverbanks, the regatta promises an unforgettable experience outdoors.

Stroll Through Boston’s Art and Culinary Scene

Elevate your experience by joining a walking tour that combines the best of Boston’s fall foliage and its captivating neighborhoods. Discover the best food in Boston and sample the flavors of the city with a North End Boston Food Tour. And for a rainy day excursion, explore Boston’s brewery scene with a guided Boston Brewery Tour.

Cheer for Your Favorite Teams

For sports enthusiasts, October brings excitement with Bruins, Celtics, and Patriots games. With TD Garden conveniently located in the heart of the city, attending a game is a breeze. For Patriots fans, the Patriot Train offers easy transportation to Gillette Stadium.

Celebrate Indigenous Peoples’ Day

Join Boston in honoring Indigenous Peoples’ Day on the second Monday of October. This weekend brims with parades, artist studios opening their doors, free museum admissions, and more. As the city comes alive with festivities, take in the cultural richness that Boston has to offer.

Celebrate Halloween

Boston wears Halloween like a crown and October is the perfect time to revel in its eerie charm. Throughout the month, the city pulses with Halloween festivities, including the renowned Ghosts and Gravestones tour. Get into the Halloween spirit while taking in the sights of the city from the trolley.

Wander Through Open Art Studios

Unlock the world of art in Boston by exploring the Fort Point Arts Community. Twice a year, artists in this vibrant community open their studios to the public. From October 13-15, 2023, engage with local artists and discover their creative processes. Dive into the world of contemporary art against the backdrop of the South Boston Waterfront.

As the vibrant colors of fall unfold across Boston, we invite you to experience the city’s charm and lively events. From the Latin-inspired cuisine at Para Maria to the panoramic views of Lookout Rooftop, these dining experiences are the perfect way to end the day’s adventures.