August 5, 2025
September in the City: Fall Colors, Festivals & Local Flavor in Boston
by Sadie Burchard
As summer winds down, Boston embraces a new kind of energy and the city pulses with a perfect blend of late summer vibrancy, and early autumn charm. Students flock back to campus, the leaves begin their transformation, and the air becomes crisp. Whether you are chasing festivals, food, or foliage, there is no better place to experience it all than The Liberty Hotel — a bold historic retreat nestled in the heart of Boston’s most picturesque neighborhood: Beacon Hill.
Here is your curated guide to the best of Boston this September — and why the Liberty Hotel is your ideal launchpad for every moment.
Labor Day Weekend: River Walks, Concerts, and One Last Taste of Summer
August 30th – September 2nd
Boston sends off summer with a weekend of free outdoor fun. Head to the Charles River Esplanade for open air concerts and scenic walks or catch one of the final Boston Harbor sightseeing cruises of the season for the best views of Boston.
Just steps from the scenic Charles River Esplanade, The Liberty Hotel is the perfect home base for a quintessential Boston weekend. Whether you’re seeking stunning waterfront views or a bit of outdoor adventure, it’s all right outside our door. Guests of The Liberty can enjoy complimentary kayaking at Boston Community Boating – just a short stroll away. Simply show your room key for access, and spend the afternoon paddling along the Charles River, soaking in skyline views and the city’s energy from the water.
After your excursion, head back to The Liberty and unwind in style. Enjoy a handcrafted cocktail at The Liberty Bar, located in our dramatic 90-foot rotunda, or settle into a memorable meal at CLINK., our signature restaurant known for its creative takes on New England cuisine.
Feast of San Gennaro in the North End
September 5th– 7th
The beloved Feast of San Gennaro brings the flavors and traditions of Italy to the North End. Expect live music, cannoli eating contests, food vendors, and cultural pride lining the cobblestone streets. It is a can’t miss celebration of one of Boston’s most iconic neighborhoods.
Boston Arts Festival
September 6th – 7th | Christopher Columbus Waterfront Park
Celebrate Boston’s creative spirit at the Boston Arts Festival, where local artists and performers highlight their unique talents with a scenic harbor backdrop. It is a vibrant, family-friendly event perfect for those who love to browse and draw inspiration.
Red Sox at Fenway Park
All Month Long
There is nothing quite like catching a game at Fenway Park – the oldest Major League Baseball stadium in America. With it’s iconic Green Monster and timeless charm, Fenway is a living piece of baseball history. September is prime time for Red Sox baseball, especially during the thick of their exciting playoff race. Whether you’re a diehard fan, or just looking for an unforgettable Boston experience, a night at the ball game is pure magic.
Best of all, Fenway is just a quick T ride away from The Liberty.
Open Newbury Street
Car-Free Sundays: September 7th, 14th, and 21st
For three Sundays in September, Newbury Street, Boston’s premiere shopping and dining street, goes completely car free. Stroll from boutique to café, explore sidewalk pop-ups, and enjoy the city’s Back Bay charm. The Liberty is just a walk away, through one of Boston’s most picturesque landmarks, The Boston Common or Public Garden.
Freedom Trail Walking Tour
Daily
September’s cooler temperatures are ideal for a guided Freedom Trail tour. Walk the path through 16 historic sites, from Boston Common to Faneuil Hall, and learn about the revolution that shaped a nation— all just a short walk from The Liberty.
SoWa Open Market
Every Sunday
Located in the South End, the SoWa Open Market brings together local artists, vintage vendors, food trucks, and more every Sunday. It’s the perfect way to spend a lazy Sunday.
Don’t forget to take advantage of our Sunday Funday Package, complete with overnight valet parking, and a 50-dollar food and beverage credit to indulge in at Clink. And The Liberty Bar. Available for one-night stays from Sunday-Monday.
Boston Local Food Festival
September 14th | Rose Kennedy Greenway
Eat your way through the best of New England at the Boston Local Food Festival. This one-day event features farm fresh dishes, sustainable food vendors, and chef demos right on the greenway.
From its rich history and architectural grandeur to its unbeatable Beacon Hill Location, The Liberty Hotel offers more than just a place to stay. Whether you are visiting for a festival, a baseball game, or just a romantic fall weekend, The Liberty makes every moment feel extraordinary.