15 Best Things to Do in Dedham (MA)

Written by Jan Meeuwesen
Updated on
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Incorporated as long ago as 1636, Dedham is the seat of Norfolk County, with an historic center commanded by a courthouse from 1820.

In Dedham you can visit a residence known to have been built around the time the town was founded. The Fairbanks House dates to around 1637, and preserves a rare amount of original detail.

The town also has one of the oldest historical societies in the United States, founded 1859, and based in a Romanesque Revival building in the historic center.

To go with its volumes of history, Dedham has big swaths of nature, west at the prominent Wilson Mountain, and east along the banks of the manmade Mother Brook, the oldest man-made waterway in the United States, also dating to the 1630s.

1. The Fairbanks House

Fairbanks HouseSource: User:Magicpiano / Wikimedia | CC BY-SA 4.0
Fairbanks House

Dedham is the home of the oldest-surviving timber-frame house in North America to be verified by dendrochronological testing.

This incredible slice of history was built around 1637 by the Puritan settler, Jonathan Fairbanks (1594-1668), who had arrived in Massachusetts in 1633.

Almost as impressive, the house stayed in the Fairbanks family across eight generations up to the 20th century.

The building is an invaluable architectural document, surviving with relatively few alterations and retaining an unusual number of original features, providing endless information for historians about life in the earliest years of European settlement in the Northeast.

The Fairbanks House has been an historic house museum since 1905, and knowledgeable docents provide in-depth guided tours of the interior, while you can also book a tour of the Colonial Kitchen Garden, growing culinary and medicinal plants from the period.

2. Dedham Village Historic District

Norfolk County CourthouseSource: quiggyt4 / shutterstock
Norfolk County Courthouse

The old heart of Dedham is both a dynamic commercial area and a place of real historical interest. To really do this place justice, you can embark on an hour-long self-guided walking tour, with a guide published by the Dedham Historical Society.

Mostly clustered on High Street, Village Avenue and Church Street are more than 35 stops where you can delve into almost 400 years of history.

Along with the Fairbanks House, one of many residences of note is the Samuel Dexter House (1761), built for a future member of the Massachusetts Congress, and serving as the headquarters of General George Washington for a night in April, 1776, following the evacuation of Boston.

The big landmark meanwhile is Norfolk County Courthouse (1820), built in the Greek Revival style, and declared a National Historic Landmark in 1972.

Nowadays, the intersection of Washington Street and High Street is a food and drink hotspot, with cafes, bars, bakeries, a tavern, an ice cream parlor, and spots for Greek, diner food, Mexican, Caribbean fusion, BBQ and more.

3. Dedham Museum & Archive

Dedham Museum & ArchiveSource: Daderot / Wikimedia | CC0
Dedham Museum & Archive

Dedham’s historical society is a major organization with its own purpose-built headquarters and a history reaching back to 1859.

The society’s library comprises more than 10,000 volumes, and the collection of artifacts includes the oldest chair made in America (1652), and paintings by Gilbert Stuart and John Constable.

The Dedham Museum & Archive is right in Historic Dedham Square, in a fine Romanesque Revival building completed in 1887.

You can view pieces from the society’s immense collections at smartly presented temporary and ongoing exhibitions. Recent shows have dealt with slavery and abolitionism, Native American tools, and examples from the society’s collection of historic shoes.

4. Legacy Place

ShoppingSource: VGstockstudio / shutterstock

Designed like a dense urban center with busy sidewalks, Dedham’s Legacy Place is an upmarket outdoor mall, packed with stores and eateries, and enlivened by seasonal programming.

For an idea of the shopping experience you’ve got Apple, Loft, Urban Outfitters, Banana Republic, Sephora, Anthropologie, J. Crew and L.L. Bean.

For entertainment there are branches of Kings Dining & Entertainment and Showcase Cinema de Lux, both of which we’ll cover in more detail later.

The food and drink choices are in keeping with the high-end ambience, so think Sweetgreen, Shake Shack, Yard House, CAVA and a Legal C Bar for New England-style seafood.

5. Wilson Mountain Reservation

Wilson Mountain ReservationSource: Adam Gladstone / shutterstock
Wilson Mountain Reservation

The largest single open space in Dedham is on just over 200 acres, covering Wilson Mountain, which is the highest point in the town at 295 feet.

The word “mountain” might seem a bit much, but this peak sits alone, so the summit has unbroken views of the surrounding area, including the Boston skyline, a few miles to the northeast.

The park has deep stands of hardwood forest, and the surprisingly challenging hillside trails lead you over streams and past vast rhododendron bushes and spectacular granite formations.

6. Mother Brook

Mother BrookSource: Leo F Brady / shutterstock
Mother Brook

The first man-made waterway in the United States is right here in Dedham, flowing between the Charles River and the Neponset River in Boston’s Hyde Park neighborhood.

Dug by English settlers to power a grist mill in 1639, Mother Brook remained a vital source of power for Dedham’s mills until as late as the 20th century.

Today you can walk along a stretch of the brook, beginning at the picturesque Mill Pond Park in East Dedham.

From here the trail network takes you downstream, across the river through Condon Park, before switching banks again to Oakland Street as far as a former mill complex (Fourth Privilege), converted into condominiums in the mid-1980s.

7. Cutler Park Reservation

Cutler Park ReservationSource: Igal Shkolnik / shutterstock
Cutler Park Reservation

On the Charles River, this wetland preserve is mostly in Needham, but the southern end is on Dedham’s northern tip, with a parking lot on the town line along Needham St.

The 600-acre Cutler Park Reservation protects a large freshwater marsh habitat, fringed by hardwood forest.

From the Dedham side, the Blue Heron Trail alternates between lush woodland and open expanses of marsh, made navigable by a long and narrow stretch of boardwalk.

Keep heading north and you’ll eventually come to Kendrick Pond, traced by a looping trail and offering a habitat to a rich variety of birdlife, from great blue herons to hawks.

8. Dedham Community Theatre

Dedham Community TheatreSource: quiggyt4 / shutterstock
Dedham Community Theatre

Still going strong in a Georgian Revival building in the heart of Historic Dedham Square is a wonderful locally-owned independent cinema.

With two screens, Dedham Community Theatre dates back to 1927, and differentiates itself from the local Cinema de Lux multiplex by specializing in independent and foreign films.

This is a different, more personal movie experience, and it’s not unusual to be greeted by the owner serving concessions.

You can sip a glass of beer or wine as you watch your movie, and the popcorn is always hot and made fresh, with real melted butter.

9. Dedham Farmers’ Market

Farmers MarketSource: Matej Kastelic / shutterstock
Farmers Market

On Wednesday afternoons, mid-June through late October, Dedham’s farmers’ market has a perfect location at the foot of the beautiful First Church. On a typical week there may be more than 30 vendors at the market.

When we put this list together the roster included a wealth of fresh produce from nearby farms, as well as potted plants, fresh croissants, local poultry, eggs, Mediterranean pastries, scones, homemade cookies, ocean-fresh seafood, natural pet supplies, vegan ice creams and small-batch wines.

There’s always a large array of craft vendors, for all-natural beauty products, handmade jewelry, pottery, housewares and a lot more besides.

10. Showcase Cinema de Lux

Movie TheaterSource: Stockbusters / shutterstock
Movie Theater

The movie theater at Legacy Place is part of Showcase Cinemas’ upmarket Cinema de Lux brand. It’s interesting to note that there has been a cinema on this very site since 1948.

The original was the Redstone Dedham Drive-In, converted into an enclosed cinema in 1982 and replaced by the mall and the current, 15-screen all-stadium seating Cinema de Lux location in 2009.

For the ultimate entertainment experience, try to catch a show at the Showcase XPlus Laser auditorium, with the latest projection, screen and audio technology.

Following renovations a few years ago, all of the screens have reclining chairs with cup holders, while Lux Level offers in-seat dining throughout the show.

11. McGolf

Mini GolfSource: Andrey Armyagov / shutterstock
Mini Golf

This all-encompassing golf facility has a driving range, short game area and miniature golf course, accompanied by a cafe and creamery.

Using laser yardages, the driving range at McGolf has 65 divided hitting bays, almost all of which have Power Tees, while 20 are covered and heated in the winter.

Behind the range is a large, perfectly maintained green with rough and bunkers so you can perfect your short game. Families meanwhile will adore the 18 holes of miniature golf, woven into a sloping landscape of manicured shrubs, topiaries, waterfalls and even a koi pond.

Finish up with a treat, from burgers, hot dogs, clubs and fries, to scores of ice cream flavors, soft serve, sundaes, slushies and frozen yogurt.

12. Blue Hills Reservation

Blue Hills ReservationSource: FPE Photography / shutterstock
Blue Hills Reservation

Bordering Dedham to the southeast is a range of granite hills containing the highest peak between Boston and Providence.

At 635 feet, Great Blue Hill is easily reached from Dedham and commands dramatic views of the Boston skyline and harbor islands from its summit.

The peak has an interesting scientific heritage as the site of the active Blue Hill Meteorological Observatory, established in 1886 and taking groundbreaking measurements of upper atmosphere weather conditions in the late 19th century.

For an extended adventure in the 7,000-acre state park you can hike east on the Skyline Trail, connecting a chain of panoramic summits along the ridge of the Blue Hills.

13. Blue Hills Trailside Museum

North American River OtterSource: DejaVuDesigns / shutterstock
North American River Otter

Being on the west side of the Blue Hills reservation, Dedham is a stone’s throw from this fantastic museum, resting on the flank of Great Blue Hill.

The Blue Hills Trailside Museum opened in 1959 and continues to be a gateway to the Blue Hills for more than 300,000 visitors each year.

Children will be thrilled with the animal enclosures, keeping rescued species unable to be reintroduced to the wild.

Among them are several varieties of birds of prey, foxes, deer and river otters. Indoor exhibits, all filled with interactivity, go into detail on the natural history of the Blue Hills and help you identify wildlife along the trails by sight or sound.

14. Kings Dining & Entertainment

BowlingSource: Aleksandar Karanov / shutterstock

At Legacy Place you’ll find a location for this regional chain of entertainment centers. Central to every branch of Kings Dining & Entertainment is a ten-pin bowling alley, and it’s worth booking a lane in advance if you’re coming at a busy time.

Also at this venue are billiards, air hockey tables and the 1UP Retrocade, loaded with vintage arcade cabinets from the 80s and 90s.

Food and drink are also at the core of the experience, with a big choice of shareables, including quesadillas, fried brussel sprouts, fresh pretzels, buffalo chicken wontons and much more.

You can choose from a list of fancy craft cocktails, as well as local craft beer, on tap or by the bottle.

15. Flag Day Parade

Flag Day ParadeSource: Suzanne Tucker / shutterstock
Flag Day Parade

Along with Quincy, Dedham is one of the few towns to hold official events on Flag Day, June 14. The tradition was adopted as long ago as 1967, and continues to draw thousands of spectators onto the streets for a parade.

This spectacle features a slew of marching bands of all descriptions, from Dedham, neighboring communities, wider Norfolk County and the New England region.

These are accompanied by elaborate floats representing a host of organizations, clubs, businesses and services. The parade weaves through Historic Dedham Square before heading east on High Street and eventually finishing up at Dedham Pool.


15 Best Things to Do in Dedham (MA):

  • The Fairbanks House
  • Dedham Village Historic District
  • Dedham Museum & Archive
  • Legacy Place
  • Wilson Mountain Reservation
  • Mother Brook
  • Cutler Park Reservation
  • Dedham Community Theatre
  • Dedham Farmers’ Market
  • Showcase Cinema de Lux
  • McGolf
  • Blue Hills Reservation
  • Blue Hills Trailside Museum
  • Kings Dining & Entertainment
  • Flag Day Parade