This well-heeled suburb of Boston is on the map for its institutions of higher education.
The most famous is the private women’s liberal arts college, Wellesley College, which has an amazing list of high-achievers among its former students, including Hilary Clinton.
The Wellesley College campus is one of the most beautiful in New England, where you’ll find an art museum with an extraordinary collection, and important contemporary art exhibitions.
Wellesley’s bustling downtown area is on the halfway mark of the Boston Marathon, and for decades the Wellesley College students have created the Scream Tunnel to give a boost to runners.
1. Wellesley Square
Served by an MBTA station on the Framingham/Worcester Line, Wellesley’s main commercial district is a percolating hub for shopping, dining and culture, with more than 100 local businesses.
Laced with greenery at Hunnewell Park, Central Park, Church Park and Morton Park, Wellesley Square is the kind of walkable downtown that most communities aspire to have, with a steady flow of public events all year round.
For a snapshot of what to expect, Wellesley Square has boutiques, galleries, florists, handmade gift shops, a toy shop, a book shop and loads more. The dining choices are too many to mention, spanning all palates, from pizza to vegan dining.
2. Wellesley College
One of the top liberal arts colleges in the United States, Wellesley College is the largest employer in the town and counts Hillary Clinton, Madeleine Albright, Diane Sawyer and Cokie Roberts among its astonishing list of alumni.
Classes commenced in 1875, and the densely wooded campus has a fabulous setting on the northern shore of Lake Waban.
Paths snake through groves of conifers and hardwoods and across meadows, with fine brick and stone buildings like Tower Court perched on the rolling hills.
Unless you’re a prospective student, the main reasons to visit are for the exceptional Davis Museum, and for the Wellesley College Botanic Gardens.
3. Davis Museum at Wellesley College
With free admission for the public, this superb art museum is part of an ensemble of arts facilities on the campus, and is linked to the Jewett Arts Center by an enclosed bridge.
With a collection first assembled in the 1880s, the Davis Museum is housed in a building from 1993 designed by Pritzker Prize-winning architect Rafael Moneo.
The museum’s scope is large, ranging from ancient artifacts, such as a mosaic excavated in Antioch, to contemporary art exhibitions. In the collection are pieces by Lavinia Fontana, Paul Cézanne, Andy Warhol, Jackson Pollock, John Singleton Copley, Ammi Phillips and many others.
Among the lineup of recent shows are solo exhibitions by the likes of Sondra Perry, Alexandria Smith, Daniela Rivera and Fatimah Tuggar.
4. Brook Path (Fuller Brook Park)
Wellesley’s most popular public park traces Fuller Brook, and its tributary Caroline Brook, for more than three miles through central Wellesley.
The Brook Path dates back to 1899, and was created partly to improve drainage in areas prone to flooding, and to offer public parkland in the heart of the town.
The park was improved during the Great Depression in the 1930s with regrading and the stone bridges that are still here. Linking with the Crosstown Trail and the Guernsey Path, the Brook Path is part of Wellesley’s large trail system, helping you reach a host of places without a car.
The trail passes through secluded woods, wetlands and open grass, but also serves more developed areas like the recreation facilities at Hunnewell Fields.
5. Massachusetts Horticultural Society’s Garden at Elm Bank
Southwest of Wellesley, on a loop in the Charles River there’s a 182-acre reservation on a former country estate, listed on the National Register of Historic Places.
The prime attraction at Elm Bank is the 36-acre Elm Bank Horticulture Center, home of the Massachusetts Horticultural Society. There’s a patchwork of magnificent gardens here, all framed by the Colonial Revival manor house from 1907.
Some of these spaces, including the Italianate Garden, were first laid out by Percival Gallagher of the famed Olmsted Brothers firm.
Other highlights include the Daylily Garden, in bloom in mid-summer, the Alan Peyton Rhododendron Garden, the Shade Garden, the Trial Garden, Weezie’s Garden for Children, the Teaching Herb Garden, and the Historic Daffodil and Native Plant Garden, a spring spectacle for more than 20 years.
6. Wellesley College Botanic Gardens (WCBG)
Open to the public on the north side of the Wellesley College campus is a botanical garden, with more than 1,500 taxa from over 150 distinct plant families.
The roots of the gardens go back to the early 1850s, with the planting of the H. H. Hunnewell Arboretum, named for Wellesley resident and credited with popularizing rhododendrons in the United States in the 19th century.
Later in the century came the delightful Alexandra Botanic Garden, with specimen trees and shrubs from across the globe, on the banks of the Silver Thread brook and Paramecium Pond.
Inside, the new Global Flora Conservatory at the Margaret C. Ferguson Greenhouses (opened 2022) is a “showcase of living beauty highlighting plant form”, and a nexus point for interdisciplinary science research and teaching.
Finally, on the slope below the Whitin Observatory is the Edible Ecosystem Teaching Garden, mimicking the properties of a natural ecosystem but producing food and substances/materials useful to humans.
7. Hunnewell Park
One of the largest public parks in the whole town is right next to Wellesley Square, and is possibly the prettiest location in Wellesley.
Hunnewell Park is an oasis of rolling lawns and mature trees commanded by the beautiful Town Hall (1883), placed on the National Register of Historic Places.
This is an interesting blend of styles, combining Richardsonian Romanesque, Mannerist gables and porticos, and Chateauesque elements in the steeply pitched hipped roof and corner towers.
Hunnewell Park is for passive recreation, with benches, picnic tables, paths and a gorgeous little pond, all with a few steps of Wellesley Square’s shops and eateries.
8. Wellesley Symphony Orchestra (WSO)
Wellesley has a regional community orchestra that was founded as long ago as 1948. At the time of writing, the WSO was helmed by Music Director/Conductor Max Hobart, a long-time member of the Boston Symphony Orchestra.
The orchestra is responsible for a number of programs in the area, elevating composers and new music, encouraging young talent and appreciation for classical music.
For the past 40 years the Wellesley Symphony Orchestra has been orchestra-in-residence at Wellesley Community College, with around six performances a year, October through May.
9. Elm Bank Reservation
The surrounding estate at Elm Bank Reservation has a long history, going back some 300 years.
The name comes from the elm trees that were planted along the bank of the Charles River in the mid-18th century.
Away from the gardens you can hike out into the reservation, along a broad, 2.6-mile looping trail that follows the riverbank through remote woodland.
The trail is on level ground, and suitable for families, while dogs are permitted in this part of the reservation, but not in the gardens.
10. Weston Ski Track
The DCR operates this extensive cross-country skiing and snowshoeing area, just northeast of Wellesley, along the Charles River.
In a normal season, the Weston Ski Track is open December through March, and has 15 kilometers of natural groomed trails, and a snowmaking area with a guaranteed 2.5 km.
Night skiing afforded by LED lighting, and everything you need is available from the ski shop (purchase or rental).
This facility is a hub for a number of competitive Nordic ski programs, while you can come for solo and group ski lessons, which are rarely canceled, because of the snowmaking facilities.
11. Morses Pond Beach
Right on the town line in the west of Wellesley, Morses Pond is linked to Wellesley Square and Wellesley College by the Crosstown Trail, on the course of the Cochituate Aqueduct.
A local destination for water activities like boating, fishing and swimming, the pond covers 100 acres, and on the east side is extensive wooded parkland and Wellesley’s favorite public beach, complemented by a picnic area and a pavilion with a BBQ.
Morses Pond Beach has lifeguards on duty daily throughout the school summer break. You’ll need a pass to use the beach, and season passes are available to non-residents.
12. Babson College
The 350-acre campus for this high-ranking private business school is in the east of Wellesley in the Babson Park area.
Contiguous with the Olin College of Engineering and dating back to 1919, Babson College is laid out like a classic New England college campus, with fine Georgian Revival architecture, flowing lawns, soaring trees and several state-of-the-art modern buildings.
You can download a map for a self-guided tour, but there are plenty of other reasons to visit, not least for a packed agenda of conferences, forums and other events throughout the year.
You can also catch performing arts at the 441-seat proscenium Carling-Sorenson Theater, while the school has 22 varsity sports teams.
13. Boston Marathon
On the third Monday of April (Patriot’s Day) tens of thousands of runners make their way through Wellesley along Central Street and Washington Street on the Boston Marathon.
Wellesley Square is at the exact halfway point of this storied race, dating back to 1897 and officially the oldest annual marathon in the world.
Thousands of people take to the streets to cheer on the runners. For decades, Wellesley College’s students have been responsible for the Scream Tunnel, producing a formidable wall of noise along a quarter-mile of the course that can be heard from a mile away.
14. Wellesley Wonderful Weekend
The annual curtain raiser for the summer season in Wellesley is this weekend of festivities a week before Memorial Day.
Organized by the Wellesley Celebrations Committee, the event’s mainstay on the Saturday is the annual Veterans Parade, which dates back more than half a century.
This is part of a packed program of goings-on from Thursday to Sunday, with a fun fair at Hunnewell Field, a pooch parade, an outdoor movie screening, and a fireworks show on the Sunday night to round the whole thing off.
15. Summer Concert Series
Wellesley Town Hall serves as the perfect backdrop for free live music performances all through the summer.
These shows usually take place on Wednesday evenings from late June to mid-August, and feature tribute bands playing everything from jazz classics to classic rock and Motown.
Active entertainment is also provided to keep kids busy. Meanwhile on Friday evenings there’s a whole season of child-friendly outdoor movies here, and a few picks from when we wrote this list were Finding Nemo, Sonic the Hedgehog and A Bug’s Life.