FALL BUCKET LIST
EXPLORE BOSTON THIS FALL: 15 MUST-DO ACTIVITIES
Get ready to embrace fall in Boston with our ultimate checklist: stunning fall foliage? Check. Outdoor fun? Absolutely. Fall festivals galore? You bet! Whether you're a leaf-peeping enthusiast, Oktoberfest aficionado, or die-hard sports fan, this guide has you covered with 15 essential activities to experience in Boston this fall.
EXPLORE BOSTON’S BEER SCENE
It’s Beer Season! Sam Adams Brewery is throwing its annual Oktoberfest celebration from September 22nd to 24th, featuring traditional and innovative brews. With stein-hoisting competitions, live music, and delicious bites, it's the perfect way to kick off the fall. And don’t miss the VIP Oktoberfest Beer Dinner on September 21st to get an exclusive taste of the festivities.
​Not a Sam Adams fan? Check out Boston’s vibrant beer scene by visiting Trillium, Dorchester Brewing, or City Brew Tours for a curated journey through the city's finest breweries.
VISIT ICONIC ACADEMIC LANDMARKS
Take in the autumn charm of Boston's academic treasures. Whether it’s exploring the historic Boston Public Library or the Boston Athenaeum, a stroll through these institutions is a fall must. For the ultimate Ivy League experience, don’t skip Harvard Yard and the surrounding Harvard Square in Cambridge. Cozy up in a café, or dive into a bookstore—it's all part of the experience.
EMBRACE THE OUTDOORS
As the leaves turn, Boston’s parks and outdoor spaces come to life. Take a walk through the Boston Public Garden or along the Charles River Esplanade. Rent a kayak, bike through one of Boston's neighborhoods, or even take a ferry to the Boston Harbor Islands. The city’s outdoor spaces shine in the fall, making it the ideal time to explore.
SHOP THE OUTDOORS
Love fall shopping? Wander down the charming streets of Beacon Hill, head to Quincy Market, or check out the farmers markets in Copley Square and SoWa. From pumpkins and gourds to unique crafts, there’s no shortage of seasonal finds to explore.
HEAD TO CAMBRIDGE
Cambridge is a must-visit during fall. Beyond its academic prestige, the city offers tons of attractions, restaurants, and cultural spots. Take in the beauty of Harvard Square, visit local breweries, or check out Graffiti Alley in Central Square for an artistic twist.
ATTEND THE HEAD OF THE CHARLES REGATTA
The world’s largest three-day rowing event takes over the Charles River in October, bringing in athletes and spectators from around the globe. Even if you're not rowing, it’s a thrilling Boston fall tradition to watch the races and take in the vibrant energy along the river.
DAY TRIPS BEYOND BOSTON
Take your fall exploration outside the city. Visit Salem for Halloween festivities, explore historic Lexington and Concord, or enjoy the beauty of Cape Cod and its seasonal offerings. New England is known for its fall foliage, so make sure to venture out for some leaf-peeping or pumpkin picking.
CHEER FOR BOSTON'S SPORTS TEAMS
Fall is prime sports season in Boston. Catch a Patriots game at Gillette Stadium or watch the Celtics and Bruins at TD Garden. College football and soccer fans also have plenty to cheer about, making it a great time to get in on the action.
TAKE A WALKING TOUR
Explore Boston’s history and culture on foot with a walking tour. Whether you want to follow the Freedom Trail, discover the hidden gems of Beacon Hill, or stroll through filming locations, there’s a tour for every interest this fall.
INDULGE IN BOSTON'S SEAFOOD
Fall is one of the best times to savor Boston’s seafood. Head to a local spot for oysters or enjoy a classic New England lobster roll. Whether you’re dining at a waterfront restaurant or at a pop-up seafood shack, you’ll find the city’s seafood offerings to be exceptional.
DISCOVER NEIGHBORHOOD GEMS
Beyond the big tourist attractions, Boston’s neighborhoods are filled with hidden gems. Explore unique bookstores, sip coffee at neighborhood cafés, or visit local speakeasies. Neighborhood favorites like Beacon Hill Books & Café and Reign Drink Lab offer unique experiences for those looking to uncover the city’s best-kept secrets.
EXPLORE BOSTON’S MUSEUMS
From the Museum of Fine Arts to the Isabella Stewart Gardner Museum, Boston’s museums are perfect for a cultural autumn experience. If you're an art lover, don’t miss the Institute of Contemporary Art in the Seaport, or visit the JFK Presidential Library for a dose of history.
ENJOY A CONCERT OR SHOW
Boston’s concert and theater venues light up in the fall. Check out the schedule at TD Garden, MGM Music Hall, or the Citizens Bank Opera House. Whether it's live music or a Broadway show, there’s something for every taste.
EXPERIENCE HAUNTED BOSTON
Boston’s spooky side comes alive in the fall. Take a haunted tour or visit one of the city’s most haunted locations. Feeling adventurous? Head to Salem for a full-on Halloween experience.
TAKE A FOOD TOUR
Explore Boston’s neighborhoods through their diverse food scenes. From the pizza of the North End to the dumplings of Chinatown, or even a chocolate tour in Harvard Square, these food tours blend culture, history, and delicious flavors into one unforgettable experience.
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This fall, Boston is brimming with activities and events that capture the magic of the season. So grab your scarf, head out, and start checking off your Boston Fall Bucket List!