There’s something about fall in Boston that feels both grounded and invigorating. The city’s deep history and walkable neighborhoods take on a new energy as trees turn golden, the air cools, and visitors arrive in droves. September and October are especially busy, and for good reason. It’s the perfect time to explore, and from our home on Beacon Hill, The Whitney Hotel Boston is ideally situated to experience the season’s best.

Take in the Fall Colors

Just steps from The Whitney, Boston Common, and the Public Garden offer a front-row seat to the changing leaves. In Boston Common, the oldest city park in the country, wide pathways lined with historic trees glow in fall light. The Public Garden, more intimate in scale, is known for its quiet charm and swan-dotted lagoon.

Looking to stretch the view? The Charles River Esplanade is just across the way, with riverside walking paths and sweeping foliage views. Or venture to the Arnold Arboretum in Jamaica Plain; its vibrant fall display makes it worth the short trip.

Cruise in a Swan Boat

The Swan Boats are one of Boston’s most iconic warm-weather experiences, and fall marks the tail end of their season. Operated by the same family since 1877, these pedal-powered boats glide quietly through the lagoon in the Public Garden, offering a peaceful and slightly whimsical way to take in the fall colors. It’s a uniquely Boston tradition that visitors of all ages enjoy.

Visit a Local Apple Orchard

Roughly 17 miles from the city, Belkin Family Lookout Farm in South Natick offers classic autumn experiences in a historic setting. This working farm dates back to the 1600s and today welcomes guests to pick apples, Asian pears, and pumpkins. Younger visitors can enjoy a corn maze, play area, and bounce pad, while adults can relax at the onsite taproom, known for its farm-made cider and beer. With frequent live music and trivia nights, it’s a lively day trip that still feels true to the season.

Show Off Your Costume at the Little Monstah Mash

October 26

Each year, a crowd of costumed kids gathers for the Little Monstah Mash, a cheerful event at The Whitney Hotel, filled with thrills and plenty of Halloween spirit. Expect creative costumes, spooky activities, and an easygoing atmosphere that brings together families from all over Boston. It’s a great way to celebrate the season, especially for younger guests.

Bring Your Pup to Howl-O-Ween

October 30

Halloween fun extends to our four-legged guests at Howl-O-Ween, a spirited pet costume parade held right here in Boston. Dogs wear everything from taco shells to superhero capes as they strut alongside fellow pups and pet parents. With photo ops and a festive atmosphere, it’s a feel-good event loved by locals and visitors alike. 

Savor Fall Flavors at Peregrine

Right here at The Whitney, Peregrine offers a seasonal menu inspired by Coastal European traditions with a New England flair, blending regional influences into both the ingredients and the philosophy of the kitchen. The restaurant’s intimate atmosphere makes it a natural fit for fall, when slowing down and savoring good food feels especially appealing. Peregrine’s name, derived from both the migratory bird and the spirit of travel, speaks to the journey each guest takes through the menu.

Enjoy a Dazzling Evening at Boston Lights

Through November 2

Franklin Park Zoo’s Boston Lights returns this season with its signature display of larger-than-life lanterns and creative light installations. Visitors will wander through a glowing forest, floral tunnels, and undersea-inspired displays, all crafted with care and imagination. The event also pays tribute to traditional Chinese lantern-making, with pandas, peacocks, dragons, and more lighting the way. 

Fall in Boston feels like a celebration, from its tree-lined streets to its packed calendar of seasonal happenings. At The Whitney, we love this time of year and the energy it brings to Beacon Hill. Whether you’re here to catch the foliage, sample local flavors, or join a Halloween parade, autumn is an invitation to experience the city in a whole new way. We’re glad to be your home while you explore it.