15 Best Things to Do in Westwood (MA)

On the western flank of the Blue Hills, Westwood is a leafy suburban town that broke away from its neighbor, Dedham, in the late 19th century.

For a community of 16,000, Westwood is spread across a big area, with a lot of land set aside for conservation.

One large reservation is managed by the private Hale, belonging to a non-profit, with roots in the early 20th century as a scout reservation.

Hale has a large swath of woods and ponds for summer camps and programs, but is also open to the public for low-impact recreation.

In an affluent corner of Greater Boston, there are upscale shopping developments in Westwood and Dedham, and a smattering of old estates and farms that have become reservations with elegant gardens, barnyard animals and a profusion of songbirds in summer.

1. Hale

With year-round educational programs and summer camps, Hale is a private non-profit organization with more than 1,100 acres of natural land in Westwood and neighboring Dover.

In summer this is an ACA-accredited day camp, offering typical camp activities for a range of age groups.

The public is free to use this land for passive recreation like hiking, mountain biking, and horseback riding, along some 20 miles of trails.

These paths take you past four bodies of water, including the stunning Noanet Pond. More activities, like swimming, boat rentals, and camping are available if you’re taking part in Hale’s various family programs.

2. Buckmaster Pond

Formed by glacial meltwater at the end of the last Ice Age, Buckmaster Pond is an attractive fixture in Westwood’s townscape.

The pond gets its name from one John Buckmaster, an early settler in the area who died in the mid-18th century.

In the immediate post-war years there was a gravel pit on the west shore, which expanded the pond by several acres.

You can get onto the shore at three parks, to the southeast, southwest and north, with lawns, play equipment, woods and benches.

There’s a boat launch here at the Buckmaster Maple Norwood Conservation Property (358 Pond St), and a few of the fish species caught in the pond are largemouth bass, chain pickerel, brown trout and catfish.

3. Westwood Day

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

Held at Westwood High School, Westwood Day is a great springboard for local businesses, with a vendor village boasting more than 120 merchants, including an array of local food options.

There’s tons for children to do, from inflatables to face painting, a “Roaming Railroad”, pumpkin decoration, a touch a truck event, and endless games.

On top of all that you’ve got a 5k run, entertainment by local performers, and a fireworks show to kick off the event following the Westwood Wolverines football game.

4. University Station

Served by the Route 128 station (MBTA commuter rail and Amtrak), this huge mixed-use development has cropped up in the east of Westwood in the last decade.

With views of the Blue Hills to the east, University Station is made up of retail, office, hotel, and luxury residential units. For stores you’ll find the likes of Target, Nordstrom Rack, Michaels, Homesense, Wegmans and Marshalls.

Restaurant chains are sprinkled across the development, with Chipotle, Panera Bread, SmashBurger, Panda Express, Starbucks and more.

5. Westwood Public Library

Completed in 2013, the main branch of Westwood Public Library is the epitome of a 21st-century library, offering up-to-date educational, professional, and recreational resources, while promoting inclusion in a dynamic, welcoming place that is free to all.

This was originally founded in 1895 as a branch of the Dedham Public Library, and the current modern building is roughly on the same site, although the historic Colburn School building had to be moved from its original location to make way.

The library has collections, facilities and programs for all ages, but is particularly useful for parents with younger children thanks to the spacious and secluded Barbara Lloyd Hayes Children’s Library.

6. Colburn School–High Street Historic District

Along High Street, from numbers 349 to 390, you can take a moment to sample some of Westwood’s history. Most of the town’s civic functions are situated on or near this stretch of road, along with some 40 historic residences.

Most of these had been standing long before Westwood was incorporated as a town in 1897, while 19th-century barns are a reminder of its rural past.

The standout building, for which the historic district is named, is the Colburn School (668 High St), constructed in the Second Empire style in 1874.

A short way north is the Classical Revival Town Hall (580 High St), completed in 1910 and state-of-the-art for the time, with modern sanitary facilities, steam heat and electric lighting.

7. Legacy Place

On the other side of I-95 in Dedham, Legacy Place is an urban-style open-air shopping and dining destination. In keeping with the area, the stores here are aimed at the upper end of the market, combined with lots of mall mainstays.

For an outline, a few tenants include Apple, Urban Outfitters, Anthropologie, Banana Republic, L.L. Bean, Gap, Sephora, Whole Foods, J. Crew, LOFT, and Francesca’s.

For entertainment there’s the high-end, 15-screen Showcase Cinema De Lux, with recliners and in-theater dining, as well as Kings Dining & Entertainment, which blends a 10-pin bowling alley with a bar & restaurant.

Among the other food picks at Legacy Place are chains like Shake Shack, CAVA, Legal C Bar, and Yard House.

8. Lowell Woods

There’s a big parcel of town-owned conservation in the north of Westwood, where you can ramble through almost 300 acres of upland woods and wetlands along Purgatory Brook.

Lowell Woods is a patchwork of four conservation properties, all threaded by three blazed trails (Blue, Red and White). What’s fascinating is that these paths are actually historic roads, traveled for generations before motorized transport.

Perhaps the prettiest scene is where the Blue Trail crosses Purgatory Brook over a cute footbridge.

9. Powisset Farm

Adjoining the Hale Reservation, there’s a history of agriculture at Powisset Farm reaching back to the 17th century.

The Trustees of Reservations runs a CSA program here, with a teaching kitchen, farmstand and barnyard animals, which children will adore.

Away from the cultivated land, a trail runs through upland woods, over brooks, past vernal pools and through wetlands.

On your walk you might catch sight of wild turkeys, white-tailed deer, and bobolinks, which nest in the grasslands.

One of the programs at Powisset Farm is a summer camp, in which kids can experience the joys of rural life, from tending to animals, to managing crops and learning some basic food preparation.

10. Rocky Woods Reservation

The Trustees of Reservations looks after this 500-acre tract of woodlands to the west of Westwood.

Water is ever-present at Rocky Woods, thanks to the reservation’s unique situation, partly in the Neponset River and Charles River watersheds.

There are wetlands throughout the landscape, which are a habitat for the likes of painted turtles, beavers and bullfrogs.

Five man-made ponds are dotted around the property, the largest of which is Chickering Pond, encircled by a ¾-mile loop.

The highest point in Rocky Woods is the summit of Cedar Hill (435 ft) at the northeast end, for a far-reaching vista over the reservation to the southwest.

11. Eleanor Cabot Bradley Estate

You can take a leisurely stroll at another Trustees of Reservations property, just east of University Station on the edge of the Blue Hills.

The Eleanor Cabot Bradley Estate is a refined country retreat, created for Dr. Arthur Tracey Cabot, who came from Boston’s prominent Cabot family.

He hired Charles A. Platt (1861-1933) to design the house and gardens, which were later enhanced with ponds, specimen trees, a greenhouse, art studio and sunken camellia garden by his niece, Eleanor.

In 1989, she bequeathed the estate to the Trustees of Reservations, and in spring and summer the formal gardens are not to be missed for their multitude of tulips, lilies, azaleas, rhododendrons, dogwood, roses and blooming perennials.

12. Lambert’s Rainbow Market

Established some 70 years ago, Lambert’s is a local chain of markets, with locations in Dorchester and at the Rainbow Square shopping center in Westwood.

This is a family operation now in its third generation, and what started out as a fruit and vegetable market has evolved into something bigger.

You’ve got a New York-style deli, salad bar, and prepared foods including a mouthwatering menu of subs, wraps and calzones. A row of shaded picnic tables out front makes this a hassle-free dining spot in the warmer months.

You can also pick up groceries, both everyday and exotic, and there’s a garden center attached for flowers, Christmas trees and gardening accessories.

13. Adams Farm

Within five minutes of Westwood you can reach some 700-acres of publicly accessible land in nearby Walpole.

The largest individual parcel here is the town-owned Adams Farm, which is a first-rate place for a hiking trip, with ten miles of trails through woods and fields, where you’ll come across old stone walls and benches for distant views.

In spring there’s a symphony of birdsong in the woods and rolling meadows, with breeding species including bobolinks, tree swallows, and eastern bluebirds.

Adams Farm is on the flightpath for migrating monarch butterflies, and the specially designed Butterfly Garden is magical from mid-summer.

14. Blue Hills Reservation

Rising just east of Westwood are the Blue Hills, set within a 7,000-acre reservation and containing the highest peak in the Greater Boston area.

That summit, Great Blue Hill (635 ft), is easy to get to from Westwood, and commands views of the entire metropolitan area.

In the 1880s, this peak was chosen for the Blue Hill Meteorological Observatory, which played a crucial role in early meteorological science, and is still active today, both as a research site and visitor attraction.

There’s tons to do in the reservation, whether you’re hiking along this chain of 22 hills, visiting the summer beach at Houghton’s Pond, skiing at the Blue Hills Ski area, or acquainting yourself with the range’s ecology and history at the child-friendly Blue Hills Trailside Museum.

15. Firefighter’s Foam

One of the more unique annual traditions in Westwood is staged in July by the local fire department.

Just for kids, Fireman’s Foam involves a couple of water cannons and a lot of harmless dish detergent, turning the grounds of Sheehan Elementary School into a foamy wonderland. The mass of foam reaches several feet in height, and kids dive in up their heads.

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