15 Best Things to Do in Westwood (MA)

Located on the western slopes of the Blue Hills, Westwood is a leafy suburb that split from neighboring Dedham in the late 1800s.

A community of 16,000 people, Westwood covers a large area, with much land set aside for conservation.

The large reserve is managed by the private organization Hale, is owned by a non-profit organization, and has its roots as a Boy Scout reserve in the early 20th century.

Hale has extensive forest and pond areas for summer camps and programs, but is also open to the public and offers recreational opportunities.

The affluent corners of the greater Boston area include the upscale shopping areas of Westwood and Dedham, as well as a number of old mansions and farms that have been turned into sanctuaries with elegant gardens, stable animals, and plenty of songbirds in summer.

1. Colburn School–High Street Historic District

From 349 to 390 along High Street, you can learn about Westwood’s history. Most of the city’s public facilities are located on or near this street, as are about 40 historic homes.

Most of these were built long before Westwood was incorporated as a town in 1897, but the 19th-century barns are a reminder of the country’s past.

The notable building that gives this historic district its name is Colburn School (668 High St), built in 1874 in the Second Empire style.

A little further north is the Classic Revival City Hall (580 High St), completed in 1910. This town hall was state of the art for its time with modern plumbing, steam heating, and electric lighting.  

2. Legacy Place

Located across Interstate 95 in Dedham, Legacy Place is an outdoor urban shopping and dining destination. Tailored to the area, the shops here are geared toward the top end of the market combined with many of the major malls.

Overview: Tenants include Apple, Urban Outfitters, Anthropologie, Banana Republic, and L.L. Bean, Gap, Sephora, Whole Foods, J.Crew, Loft, Francesca’s.

Entertainment is provided by the premier Showcase Cinema Deluxe with 15 screens, lounge chairs, cinema dining, and Kings Dining & Entertainment, a combination bowling alley, bar, and restaurant. Legacy Place also has chains like Shake Shack, CAVA, Legal C Bar, and Yard House.  

3. Lowell Woods

North Westwood has a large city-owned nature reserve where you can hike nearly 300 acres of highland forest and wetlands along Purgatory Brook.

Lowell Woods is made up of a patchwork of four nature reserves, each intersected by his three signposted trails (blue, red, and white). What’s interesting is that these trails are actually historic roads that were traversed many generations before automobile traffic.

Perhaps the most beautiful scene is when the Blue Trail crosses Purgatory Brook over a beautiful footbridge.  

4. Powisset Farm

The farming history of Powisett Farm, adjacent to the Hale Reservation, dates back to the 17th century.

Here, the Reservations Administration runs its CSA program, complete with educational kitchens, farm stands, and farm animals that kids will love.

Away from the cultivated fields, trails meander through upland forests, cross streams, past spring-fed ponds, and through wetlands.

As you walk, you might spot wild turkeys, white-tailed deer, and bobolinks nesting in the grasslands.

One of Powisett Farm’s programs is Summer His Camp, where children can experience the joys of country living, from caring for animals to tending crops to learning to prepare basic meals. 

5. Rocky Woods Reservation

The Reservation Management Board manages this 500-acre forest west of Westwood.

Water is ubiquitous in the Rocky Woods, thanks in part to the reserve’s unique location in the Neponset and Charles River basins.

Wetlands dot the landscape and are home to turtles, beavers, and bullfrogs.

Five man-made ponds dot the grounds, the largest of which is Chickering Pond, which is surrounded by a 3/4-mile ring.

The highest point in the Rocky Woods is the summit of Cedar Hill at the northeast end (435 feet), which offers sweeping views of the reserve to the southwest.  

6. Firefighter’s Foam

One of Westwood’s most unique annual traditions is held in July by the local fire department.

ESPECIALLY FOR KIDS: Fireman’s Foam combines two water cannons and a ton of non-toxic dish soap to transform the Sheehan Elementary School grounds into a foamy wonderland. The bubbles reach several feet in height and children dive head-first into them.

The first edition of Firefighter’s Foam took place in the 1980s and the event has become a staple of the summer. 

7. Blue Hills Reservation

Just east of Westwood rises the Blue Hills, which sits on a 7,000-acre reserve and is the tallest mountain in the Boston metropolitan area.

This peak, Great Blue Hill (635 feet), is easily accessible from Westwood and offers views of the entire metropolitan area.

In the 1880s, the mountain was chosen as the site of the Blue Hill Weather Station. Weather stations played an important role in early meteorological science and are still active as research sites and tourist attractions.

Hike this series of 22 hills, visit the summer beaches of Hortons Pond, ski at the Blue Hills Ski Area, and learn about mountain ecology and history at the Blue Hills Trailside Museum’s kid-friendly terrain. 

8. Adams Farm

Less than five minutes from Westwood is 700 acres of public land in nearby Walpole.

The largest single lot here is the town-owned Adams Farm, with 10 miles of trails through woods and fields, meeting old stone walls and benches and offering expansive views.

In spring, birdsong fills the forests and rolling meadows with breeding species such as bobolinks, swallows, and eastern thrushes.

Adams Farm is on the flight path of migrating monarch butterflies, and the purpose-built butterfly garden is magical from midsummer onwards. 

9. Lambert’s Rainbow Market

Founded nearly 70 years ago, Lambert’s is a local market chain with stores in Dorchester and Westwood’s Rainbow Square shopping centers.

This has been his family business for three generations and what started as a fruit and vegetable market has grown into something bigger.

New York-style deli, salad bar, delicious sub-menu, ready-to-eat meals including wraps and calzones. There are shaded picnic tables out front, so you can enjoy your meals even in the warmer months.

Daily groceries and exotic groceries are available for purchase, and there is also a garden center with flowers, Christmas trees, and gardening supplies. 

10. Eleanor Cabot Bradley Estate

You can take a leisurely stroll to another holding and management facility located east of University Station on the edge of the Blue Hills.

The Eleanor Cabot Bradley Estate is an elegant country retreat dedicated to Dr. Arthur Tracy Cabot From the prominent Cabot family of Boston.

He commissioned Charles A. Pratt (1861-1933) to design the house and gardens, which were later expanded by his niece Eleanor with a pond, specimen trees, a greenhouse, his studio of art, and a sunken camellia garden.

She bequeathed this land to the Reservation Board of Trustees in 1989. In spring and summer, don’t miss the formal gardens, which bloom with tulips, lilies, azaleas, rhododendrons, dogwoods, roses, and perennials.  

11. Hale

Hale is a private, non-profit organization that offers year-round educational programs and summer camps on over 1,100 acres of wilderness in Westwood and nearby Dover.

During the summer, this is an ACA-accredited day camp offering typical camping activities for different age groups.

Members of the public are free to use the land for passive recreation such as hiking, mountain biking, and horseback riding on approximately 32 kilometers of trails.

These trails take you through four bodies of water, including the beautiful Noahnett Pond. Other activities such as swimming, boat rentals, and camping are also available when you join Hale’s various family-friendly programs.  

12. Buckmaster Pond

Formed by glacial meltwater at the end of the last ice age, Buckmaster Pond is an attractive part of the Westwood cityscape.

The pond takes its name from the early settlers of the area, John his Buckmaster, who died in the mid-18th century.

Soon after the war, the pond was enlarged by several hectares with a gravel pit on the west bank.

His three parks, southeast, southwest, and north, lead to a beach with lawns, playground equipment, small forests, and benches.

Here at Buckmaster Maple Norwood Preserve (358 Pound Street), there is a boat launch, and fish species caught in the pond include largemouth bass, chain picker, brown trout, and catfish.  

13. Westwood Day

In mid-September, the town comes together to celebrate Westwood’s anniversary with two days of entertainment and family activities.

Westwood Day is held at Westwood High School and is a great starting point for local businesses. The merchant village has over 120 shops with a wide variety of local produce.

From bouncy castles to face painting, railroad roaming, pumpkin decorating, truck touch events, and endless games, there is so much for kids to enjoy.

5K, local artist entertainment, and fireworks will also kick off the event after the Westwood Wolverines football game.  

14. University Station

East Westwood has seen this large mixed-use development served by Route 128 stations (MBTA commuter rail and Amtrak) built over the past decade.

Overlooking the Blue Hills to the east, University Station consists of retail, office, hotel, and luxury residential units. Shops include Target, Nordstrom Rack, Michaels, Homesense, Wegmans and Marshalls.

Chain restaurants such as Chipotle, Panera Bread, Smashburger, Panda Express, and Starbucks are scattered throughout the property. 

15. Westwood Public Library

Completed in 2013, the department of Westwood Open Library is the exemplification of a 21st-century library, advertising up-to-date instructive, proficient, and recreational assets, while advancing incorporation in a dynamic, inviting put that’s free to all.

This was initially established in 1895 as a department of the Dedham Open Library, and the current cutting-edge building is generally in the same location, in spite of the fact that the memorable Colburn School building had to be moved from its unique area to create a way.

The library has collections, offices, and programs for all ages, but is especially valuable for guardians with more youthful children much obliged to the roomy and separated Barbara Lloyd Hayes Children’s Library.

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