Top 15 Must-Do Activities in Dedham, MA

Established as early as 1636, Dedham serves as the seat of Norfolk County, distinguished by its historic center dominated by a courthouse dating back to 1820.

In Dedham, visitors can explore a residence believed to have been built during the town’s founding. The Fairbanks House, constructed around 1637, showcases an impressive degree of original detail.

Additionally, the town is home to one of the oldest historical societies in the United States, established in 1859, located in a Romanesque Revival structure within the historic center.

Complementing its rich historical narrative, Dedham boasts large expanses of natural beauty, particularly west at the notable Wilson Mountain and east along the banks of Mother Brook, the oldest man-made waterway in the United States, also originating in the 1630s.

1. The Fairbanks House

Dedham is the site of the oldest known surviving timber-frame house in North America, as confirmed through dendrochronological testing.

This remarkable historical artifact was constructed circa 1637 by Puritan settler Jonathan Fairbanks (1594-1668), who had arrived in Massachusetts in 1633.

Notably, the house remained within the Fairbanks family for eight generations until the 20th century.

The structure serves as an invaluable architectural record, maintaining relatively few modifications while preserving a noteworthy number of original features, thereby offering historians extensive insights into life during the early years of European settlement in the Northeast.

The Fairbanks House has operated as a historical house museum since 1905, with knowledgeable guides providing comprehensive tours of the interior; visitors can also partake in a tour of the Colonial Kitchen Garden, which grows culinary and medicinal plants from that era.

2. Dedham Village Historic District

The historical core of Dedham serves as a vibrant commercial district while also offering substantial historical significance. To fully appreciate this area, one can undertake an hour-long self-guided walking tour, with a guide available from the Dedham Historical Society.

Concentrated mainly along High Street, Village Avenue, and Church Street, more than 35 noteworthy locations allow an exploration of nearly 400 years of history.

In addition to the Fairbanks House, another notable residence is the Samuel Dexter House (1761), which was constructed for a prospective member of the Massachusetts Congress and served as General George Washington’s headquarters for one night in April 1776, following the evacuation of Boston.

The prominent landmark is the Norfolk County Courthouse (1820), designed in the Greek Revival style and recognized as a National Historic Landmark since 1972.

Currently, the intersection of Washington Street and High Street has become a hub for dining and socializing, featuring cafes, bars, bakeries, a tavern, an ice cream parlor, and various culinary options including Greek, diner-style, Mexican, Caribbean fusion, BBQ, and more.

3. Dedham Museum & Archive

Dedham’s historical society stands as a prominent organization with a dedicated headquarters and a legacy extending back to 1859.

The society boasts a library containing over 10,000 volumes, with artifacts including the oldest chair made in America (1652) and artworks by renowned artists such as Gilbert Stuart and John Constable.

The Dedham Museum & Archive is situated in Historic Dedham Square within a beautiful Romanesque Revival building completed in 1887.

Visitors have the opportunity to engage with items from the society’s extensive collections through thoughtfully curated temporary and permanent exhibitions. Recent topics have included slavery and abolitionism, Native American tools, and examples from the collection of historical footwear.

4. Legacy Place

Modeled after a vibrant urban center complete with bustling sidewalks, Dedham’s Legacy Place is an upscale outdoor shopping district, featuring numerous retail outlets and dining establishments, complemented by seasonal events.

Notable shopping options include names like Apple, Loft, Urban Outfitters, Banana Republic, Sephora, Anthropologie, J. Crew, and L.L. Bean.

Entertainment opportunities are provided by establishments such as Kings Dining & Entertainment and Showcase Cinema de Lux, which will be detailed further later in the content.

The selection of food and beverages matches the sophisticated atmosphere, including options like Sweetgreen, Shake Shack, Yard House, CAVA, and Legal C Bar for New England-style seafood.

5. Wilson Mountain Reservation

The largest contiguous open space in Dedham encompasses approximately 200 acres, primarily comprising Wilson Mountain, which is the highest elevation in the town at 295 feet.

While the term “mountain” may be slightly misleading, this standalone peak provides uninterrupted views of the surrounding landscape, including the Boston skyline a few miles to the northeast.

The park features dense hardwood forests, and the surprisingly challenging hillside trails guide visitors over streams and past extensive rhododendron groves and stunning granite formations.

6. Mother Brook

Located in Dedham is the first artificial waterway in the United States, which flows between the Charles River and the Neponset River in Boston’s Hyde Park neighborhood.

Created by English settlers to operate a grist mill in 1639, Mother Brook served as an essential power source for mills in Dedham until the late 20th century.

Today, one can walk along a segment of the brook, commencing at the scenic Mill Pond Park in East Dedham.

From this point, the trail network leads downstream, crossing the river through Condon Park, and then back across to Oakland Street, extending as far as a former mill complex (Fourth Privilege), which was transformed into condominiums in the mid-1980s.

7. Cutler Park Reservation

Situated along the Charles River, this wetland preserve is predominantly located in Needham, although its southern end extends into Dedham, featuring a parking area on the town line along Needham St.

The 600-acre Cutler Park Reservation safeguards a vast freshwater marsh habitat, bordered by hardwood forests.

From the Dedham side, the Blue Heron Trail alternates between lush woodlands and open marshlands, made accessible by a lengthy and narrow boardwalk.

Continuing north leads to Kendrick Pond, which is encircled by a looping path and hosts a diverse array of avian life, including great blue herons and hawks.

8. Dedham Community Theatre

Continuing to flourish in a Georgian Revival building situated in the heart of Historic Dedham Square is a charming independent cinema.

With two screens, the Dedham Community Theatre has been operational since 1927, setting itself apart from the local Cinema de Lux multiplex by specializing in independent and foreign films.

This venue offers a distinctive and personal cinematic experience, often featuring warm greetings from the owner as they serve concessions.

Patrons can enjoy a glass of beer or wine during their viewing, as the popcorn is consistently served hot and freshly made, topped with real melted butter.

9. Dedham Farmers’ Market

Every Wednesday afternoon, from mid-June to late October, Dedham hosts a farmers’ market at the foot of the picturesque First Church. A typical market day may feature over 30 vendors.

As this list was compiled, the vendor array included a rich assortment of fresh produce sourced from nearby farms, alongside potted plants, fresh croissants, local poultry, eggs, Mediterranean pastries, scones, homemade cookies, ocean-fresh seafood, natural pet supplies, vegan ice creams, and artisanal wines.

Additionally, a wide selection of craft vendors offer all-natural beauty products, handmade jewelry, pottery, housewares, and beyond.

10. Showcase Cinema de Lux

Located in Legacy Place, this cinema is part of Showcase Cinemas’ upscale Cinema de Lux brand. Notably, a cinema has existed on this site since 1948.

The initial establishment was the Redstone Dedham Drive-In, which transitioned to an enclosed cinema in 1982, eventually being replaced by the mall and the current, 15-screen all-stadium seating Cinema de Lux location in 2009.

For an unparalleled entertainment experience, attendees are encouraged to experience a show in the Showcase XPlus Laser auditorium, featuring the latest in projection, screen, and audio technology.

Recent renovations have equipped all screens with reclining chairs featuring cup holders, while the Lux Level provides in-seat dining throughout the performance.

11. McGolf

This comprehensive golfing facility includes a driving range, short game area, and an 18-hole miniature golf course, along with a café and creamery.

Equipped with laser yardages, the driving range at McGolf features 65 divided hitting bays, the majority of which are fitted with Power Tees; 20 bays are covered and heated for winter use.

Additionally, behind the range is a large, impeccably maintained green encompassing rough areas and bunkers, allowing visitors to refine their short game skills. Families will particularly enjoy the 18 holes of miniature golf, set within a beautifully landscaped environment featuring manicured shrubs, topiaries, waterfalls, and even a koi pond.

Conclude your visit with a selection of treats, ranging from burgers, hot dogs, and fries to a diverse assortment of ice cream flavors, soft serve, sundaes, slushies, and frozen yogurt.

12. Blue Hills Reservation

Bordering Dedham to the southeast lies a range of granite hills that includes the highest peak between Boston and Providence.

Standing at 635 feet, Great Blue Hill is easily accessible from Dedham and offers breathtaking views of the Boston skyline and harbor islands from its summit.

This peak is historically significant as the site of the active Blue Hill Meteorological Observatory, founded in 1886, which conducted pioneering measurements of upper atmosphere weather conditions in the late 19th century.

Adventurers can hike eastward on the Skyline Trail within the 7,000-acre state park, linking a series of panoramic summits along the ridge of the Blue Hills.

13. Blue Hills Trailside Museum

Located on the west side of the Blue Hills Reservation, Dedham is in close proximity to this excellent museum, nestled on the slopes of Great Blue Hill.

Since its inauguration in 1959, the Blue Hills Trailside Museum has served as an entry point to the Blue Hills for over 300,000 visitors annually.

Children can enjoy extensive animal enclosures that house rescued species unable to be reintroduced to their natural habitats.

These enclosures include various birds of prey, foxes, deer, and river otters. The indoor exhibitions, rich in interactive displays, delve into the natural history of the Blue Hills, aiding visitors in identifying local wildlife by sight or sound.

14. Kings Dining & Entertainment

Located in Legacy Place, this entertainment center represents a regional chain known for its ten-pin bowling alleys, and it is advisable to reserve a lane ahead of time if visiting during peak hours.

In addition to bowling, the facility includes billiards, air hockey tables, and the 1UP Retrocade, featuring vintage arcade games from the 80s and 90s.

Dining is a central element of this experience, offering a diverse selection of sharable dishes, including quesadillas, fried Brussels sprouts, fresh pretzels, buffalo chicken wontons, and more.

Guests can choose from a variety of craft cocktails, as well as local craft beers, available on tap or in bottles.

15. Flag Day Parade

Alongside Quincy, Dedham is among the few towns that host official events for Flag Day, observed on June 14. This tradition commenced in 1967 and continues to attract thousands of spectators who gather for the parade.

The event boasts a plethora of diverse marching bands from Dedham, neighboring towns, and the broader Norfolk County and New England region.

These are complemented by elaborate floats representing numerous organizations, clubs, businesses, and services. The parade traverses through Historic Dedham Square before proceeding east along High Street and ultimately concluding at the Dedham Pool.