This page was updated fall 2024.
Our picks for things every Wellesley-ite should experience and that visitors to Wellesley should check out depending upon what time of year they’re in town.
Shopping
Wellesley has a mix of one-of-a-kind stores as well as chains, spread from Linden Square to Wellesley Square to Church Square and the Fells and Hills areas. Most of the areas are quite walkable and offer benches and places to grab a snack if you’re really on an epic shopping adventure. Clothing, toys, food and jewelry can all be had.
The Boston Marathon
Runners traverse the course from Hopkinton to Boston, hitting Wellesley smack dab in the middle. More than three miles of the course wind through Wellesley, including the infamous scream tunnel fueled by Wellesley College students. (As far as sports events in town, not to be overlooked is the annual Wellesley-Needham high school football game that takes place each Thanksgiving morning. It’s the oldest football rivalry between public schools. From what we’ve seen, the real action starts around halftime, when returning high school grads make their way over to the game, which alternates between being played in Wellesley and Needham.)
Wellesley’s Wonderful Weekend
Wellesley’s Wonderful Weekend, an annual town tradition that has been celebrated for over 50 years, usually in late May. Activities include a pancake breakfast, a military decampment re-enactment, musical performances and the annual Veterans Parade featuring the schools, antique cars, local politicians, army tanks and more. The event is topped off with a spectacular fireworks display at Hunnewell Field.
Babson College
The 4-year private business school’s campus features Georgian and other architecture, plus some quirky twists, including the giant Babson Globe, described by the school as “a freestanding globe measuring 28 feet in diameter and weighing 25 tons.” It is the centerpiece of Kerry Murphy Healey Park, a campus park located along the main drag of the campus. You seriously can’t miss it.
The park debuted in Spring 2019 in celebration of the school’s 100th birthday. The campus is also home to a tree spawned from the famous Isaac Newton tree. The Sorenson Center for the Arts hosts movies and various live performances (see BabsonARTS for more info). A skating rink offers public skating and is home to the Babson Beavers hockey teams, which frugal Wellesley parents trick their kids into believing are the Boston Bruins.
Dining
Wellesley offers a variety of eateries, from fancy to homey to chains. A slew of Asian restaurants dot the town, from sushi-and-more to Chinese to Thai. Or you can try out Italian eateries, Indian cuisine, Turkish specialties, or an old-timey diner with a Greek flair. And don’t forget those necessities — pizza, ice cream, donuts, and coffee. Wellesley’s got you covered there.
The dump
More formally known as the Recycling and Disposal Facility, since it is after all a model center for making the most of residents’ refuse. Many a home in Wellesley is furnished with items plucked from the give and take section manned by volunteers and popular among residents, including antiques dealers. You do need to be a Wellesley resident to visit, or at least go with one.
History
Wellesley’s Historical Society is the formal center of history in town, providing a rotating selection of displays honoring Wellesley’s most noteworthy citizens and happenings. But there are also ample opportunities to spy historical spots on your own in town, from the estates in the Cliff Road area, to the homes of notable Wellesley residents of the past such as poet Sylvia Plath and America the Beautiful writer Katharine Lee Bates, to markers commemorating historical events, including George Washington’s visit to town.
Walking/hiking trails
Woven into the town’s neighborhoods and streets are 25-plus miles of wooded trails, including Centennial Reservation, which offers access to Maugus Hill, one of the highest points in town. Boulder Brook Reservation can make you forget you’re in the burbs with its rocky outcroppings and great views (shown above). Other trails, like the Brook Path and Crosstown offer nice alternatives to taking the usual path along roads like Rte. 16. More from the Wellesley Trails Committee.
Summer concerts
The town and local businesses foot the bill for a series of summertime concerts in Wellesley Square and behind Town Hall. They take place on various evenings and Saturdays, bringing together young and old neighbors.
Wellesley College
Wellesley College. Note: some campus buildings are currently closed to the public due to rules put in place during the pandemic.
Frequently cited as one of the country’s most beautiful college campuses, this women’s college established in 1870 has much to offer to residents and visitors. First, there’s wandering around the campus itself, with its gothic and contemporary buildings, plus well-kept gardens and landscaping. Part of a path that loops Lake Waban is open and offers dramatic views of the school’s Galen Stone Tower and the lake itself. The school offers public access to its Davis Museum & Cultural Center, which includes ancient to modern art as well as lectures and shows. (Note: the Davis Museum is closed until Feb. 2024 for renovations.) The college’s greenhouses have provided a toasty plant-filled oasis on cold and rainy days, but the school has demolished them as part of a Global Flora project. The new greenhouses are slated to be open to the public in spring 2022. Several theater outfits at the college put on productions for audiences of all ages.