This historic coastal town on the bay side of Cape Cod was a favorite residence of sea captains in the early 19th century but has since become a summer hotspot for the wealthy. The water on the bay side is warmer than on the sea side and the waves are much calmer. If you’re looking for a family beach vacation, Brewster might just be the place for you.

Add to this the majesty of the Brewster Flats, said to be the largest tidal flat in the United States, and the scenery is breathtaking. The apartments are also educational for the kids as they can walk up to 2 miles at low tide to explore tide pools teeming with crabs, oysters, mussels, scallops, and other marine life.  

1. Cape Rep Theatre

This artist-led theater company in Brewster is based on seven scenic acres in Nickerson State Park.

The Cape Prep Theater is his atmospheric 125-seat indoor facility that dates back to his 1959 construction for summer camps.

In summer there is also a beautiful outdoor theater that seats up to 200 spectators and is the only theater of its kind on the cape.

Peak season runs from May through December and is packed with great productions, from classic Broadway musicals to new shows from up-and-coming creative talent.

During the summer months, there are shows for children during the day and shows for adults after dark. 

2. JT’s Seafood Restaurant

Cape Cod has long been known for its clam shacks. The Clam Shack is a no-frills storefront that serves New England’s favorite seafood and other delicious comfort food.

A classic example is the JT Seafood Restaurant on Old Kings Highway in Brewster. Menu highlights include hot and cold lobster rolls, clam chowder, clam strips, fish and chips, and lobster bisque.

If you can’t decide, you can also opt for the Fisherman’s Platter, which contains a little bit of almost anything. JT’s is also one of the few local spots that have 20 flavors of great ice cream, as well as froyo, soft serve, and sorbet.  

3. Crosby Mansion

On the road to Crosby Landing stands the magnificent mansion built in 1888 for entrepreneur Albert Crosby (1823-1906).

After moving to Chicago, he made a fortune manufacturing distilled alcohol, which was in high demand during the Civil War. His gorgeous 35-room home in Brewster is inspired by Chicago’s Gold Coast luxury mansion.

Albert and his wife Matilda named it “Tawasenta” after a poem by Henry Wadsworth Longfellow. “Song of Hiawatha”. The construction was so extensive that the site was sometimes connected to the Old Colony Railroad during construction.

Details include a 60-foot-tall observation tower, rich hand-carved mahogany furniture, a two-story billiards room, a grand drawing room, and his two-story building that showcases works by artists such as Childe Hassam and El Creco. Art included his gallery.

The Crosby Mansion still retains its former opulence and is open for tours on Sundays in July and August.  

4. Harbor Lights Mini Golf

If you’re traveling with kids and want an alternative experience to Brewster’s history and culture, there’s a classic seaside miniature golf course just off the Old Kings Highway.

Harbor Lights Mini Golf might be mistaken for a garden attraction, with winding paths and lush grass, shrubs, flowers, and water.

Small boulders are scattered throughout the route, and the main features are caves and ledges with waterfalls.

Skill is more important than luck on this 18-rolling hole. For a special treat, the course also offers Gifford ice cream, as well as floats, sundaes, and shakes.  

5. Brewster General Store

The Brewster General Store has been a part of local life for over 150 years and is a popular hideaway. A little bit of everything is sold here, and the front is lined with cheerful benches, serving as a casual common area.

Also worth noting is the building, first used as a church in 1852 and converted in 1866 with the introduction of the Cape Heiden Cod Central Railway.

Long windows on the sides of the building remind us of the building’s former function. Horatio, Alger, and Helen Keller, among others, were known to frequent the store, and part of its fame is due to several generations of holidaymakers visiting it.

Merchandise includes penny candies, greeting cards, local jams, toys, puzzles, board games, linens, household items, beach items, books, and more. People stop by early in the morning for freshly brewed coffee and pastries. Another summer must-see is the Brewster’s Scoop Ice Cream Stand in the parking lot. 

6. Crosby Landing Beach

All of Brewster’s public beaches are worth a visit, but Crosby Landing Beach is famous for its size and plenty of parking in the back dune parking lot. At high tide, you can lounge on the sand and swim in the gentle waves.

If you’ve never been there, you might not be prepared for the amazing views at low tide. When the tide goes out, all you can see is a sandy beach with tide pools.

The view is even more dramatic on a partly cloudy day or at dusk when the sun shines down on the pool and is probably one of the most romantic views you’ll ever see. 

7. Nickerson State Park

Massachusetts‘ first state park was established in Brewster in 1934.

This 1,900-acre landscape of kettle ponds and shrub pines was donated by Samuel Mayo, widow of his Nickerson (1830–1914), one of the founders of the First National Bank of Chicago.

Mayo died shortly after his mansion, Fieldstone Hall, burned to the ground. The park’s ponds, surrounded by pine trees, are prime spots for water activities, from swimming to kayaking.

Near the visitor center at the northern end, the Cape Cod Rail Trail traverses the property, with bike rental and repair stations along the way. There are a total of 26 miles of trails in the park, and many small campgrounds dot the banks of the ponds, with more than 400 campsites. 

8. Brewster Old King’s Highway Historic District

The Old Kings Highway (Route 6A, Massachusetts) is a famous and particularly scenic drive along Cape Cod around Cape Cod Bay.

A lot of history lives along this road that connects many quaint town centers. The route began as a Native American trail, became a wagon trail for settlers in the 17th century, and became a coveted residential area for sea captains in the 19th century.

Most of Brewster’s Old Kings Highway has been preserved as a historic district, and at its intersection with Howwich Road, you can visit the site of the town’s original development in the late 17th century.

Here you can visit the elegant Brewster Women’s Library, built in Stick style in 1868 and still in operation. Along with many of the attractions detailed in this article, the street is lined with antique shops, galleries, hobby shops, home design boutiques, and stately 18th- and 19th-century captain’s mansions. 

9. Cape Cod Rail Trail

This famous 40.5-mile railroad runs through Brewster along the cobbled trackbeds of the Old Colony Railroad, originally called the Cape Cod Central Railroad in the 1860s.

One of his first projects of its kind in America, the Cape Codrail Trail was built in the 1970s after Massachusetts acquired the right-of-way.

Brewster is best explored by bike or on foot. To the south is a typical Cape Cod landscape with cranberry bogs and ponds.

One is Long Pond, Cape Cod’s largest freshwater pond and the location of Brewster’s freshwater public swimming beach. The trail parallels the Old Kings Highway for a mile or two and enters Nickerson State Park at the northeast corner.  

10. Stony Brook Grist Mill and Museum

There is probably no more idyllic sight on Cape Cod than this historic hydro-powered flour mill tucked away in a small valley along Stony Brook.

The waterway was Brewster’s early lifeline, powering the nation’s first flour and wool mills in the late 17th century.

The building at 830 Stoney Brook Road is the last remnant of Factory Village, a trading community that emerged around the early 19th century.

The water wheel and mill are actually modern and were added as part of the restoration completed in 2009.

Come on a Saturday in the summer to watch the milling process and buy freshly ground cornmeal. In the spring, the Alewife herring migrate upstream to the factory ponds for spawning. This natural phenomenon can be seen at the fishway opposite the factory. 

11. Breakwater Beach

The closest public beach to historic downtown is minutes from the Brewster Store and Brewster Ladies Library.

Brewster Beach has two parking lots and is an attractive sandy beach surrounded by low dunes and protected by its eponymous breakwater.

At high tide, the beach becomes quite small and drops to a fairly steep sea level. It’s surprisingly warm in the middle of summer.

When the tide goes out, early or late in the morning, this is the place to head to Brewster Flats to explore the tide pools and watch the sunset in awe. 

12. Cape Cod Museum of Natural History

If you’re interested in Cape wildlife, natural history, and archaeology, there’s a family-friendly museum in Brewster next door to Stony Brook.

The Cape Cod Museum of Natural History exhibits a wide range of topics, from the 10,000 years of Stony Brook settlement to the Wampanoag Indians, colonization and early industry.

There is also an aquarium with more than 80 native species, as well as a beehive, butterfly hut, and native bird collection.

Another advantage of this museum is the outdoor area. The property covers over 80 acres, but the trail follows Stony Brook downriver to an additional 800 acres of nature reserve and Cape Cod Bay. There are many wonderful habitats to explore, including saltmarshes, pitch pine forests, beech forests, barrier beaches, and the Stony Brook shores where you can watch herring migrations in the spring.  

13. Paine’s Creek Beach

At the mouth of Stoney Creek is a beautiful rock-lined cove that is a delight to explore, especially in the summer.

Pines Creek Beach is a fun and safe place to swim at high tide and is an ideal place to start kayaking or stand-up paddleboarding.

At such times, it can be carried by freshwater currents into seawater. At low tide, this is another great place to start your adventure on the Brewster Flats. Or it’s also a great place to stroll until you reach the crystal-clear water for a swim.  

14. Brewster Whitecaps

Cape Cod is famous in baseball for the 10-team Cape Cod Baseball League, where future MLB stars play college baseball throughout the summer.

Cape Cod has organized baseball like nowhere else, and Brewster has had a team since his 1880s.

Still, the Brewster Whitecaps are a relatively recent team, entering the league in 1988 as an expansion team. Rising stars for the Whitecaps include Aaron Judge, Jeff McNeill and Kyle Hendricks.

The home of the Whitecaps is his 4,000-seat Stony Brookfield, which opened in 2006 and runs along the Cape Cod Rail Trail. The season runs from mid-June to mid-August, and Brewster has won three times in 2000, 2017, and 2021.  

15. Drummer Boy Park

A good companion for a trip to the Cape Cod Museum of Natural History is this public park right next door.

Drummer Boy Park is an open field with paved paths, benches, and mature trees. At the western end is Old Higgins Farm Windmill. This is his 1795-built windmill, which was moved to its current location in the 1970s.

Next to it is the Harris Black House, built around the same time and believed to be the last surviving primitive one-room house on the Cape.

On the other side of the park is a pavilion, which serves as a hub for numerous Sunday concerts and other outdoor public events in the summer.