This historic coastal town is on the bay side of Cape Cod, and was a residence of choice for sea captains in the first half of the 19th century, before becoming a summer hotspot for the wealthy. The water on the bay side is warmer than the ocean side, and the surf is a lot calmer, so if you’re looking for a spot for a family beach vacation Brewster may be right for you.
Added to that is the majesty of the Brewster Flats, thought to be the widest sweep of tidal flats in America, with views that will take your breath away. The flats are also educational for kids, as you can walk out for up to two miles at low tide, exploring tidal pools rich with crabs, oysters, mussels, scallops and other sea life.
1. Crosby Landing Beach
All of Brewster’s public beaches are worth visiting, but Crosby Landing Beach stands out for its size, and the amount of spaces at the parking lot in the dunes behind. At high tide, this is somewhere to lounge on the sand and take a swim in the gentle surf.
If you haven’t visited before, you may not be prepared for how spectacular the view is at low tide. When the tide withdraws there’s nothing but sand laced with tide pools as far as you can see.
The scenery is all the more dramatic on a semi-cloudy day, when shafts of sunlight illuminate the pools, or at sunset which may be one of the most romantic things you’ve ever laid eyes on.
2. Nickerson State Park
The Commonwealth of Massachusetts’ first state park was established in Brewster in 1934.
This 1,900-acre landscape of kettle ponds and scrub pine was donated by the widow of Samuel Mayo Nickerson (1830-1914), one of the founders of the First National Bank of Chicago.
Mayo died not long after his grand mansion, Fieldstone Hall, burned down. The park’s pine-ringed ponds make this a prime location for water activities, from swimming to kayaking.
Near the visitor center at the north end, the property is traversed by the Cape Cod Rail Trail, and there’s a bike rental and repair station on the path here.
There’s a total of 16 miles of trails in the park, along with more than 400 campsites, spread across numerous small-scale campgrounds, mostly on the shores of the ponds.
3. Brewster Old King’s Highway Historic District
The Old King’s Highway (Massachusetts Route 6A) is a famous, not to mention beautiful drive along Cape Cod, bending around Cape Cod Bay.
There’s volumes of history along this road, which links a succession of quaint town centers. The route started out as a Native American trail before becoming a cart path for 17th-century colonists, and a desirable residential street for sea captains in the 19th century.
Almost all of the Old King’s Highway in Brewster is preserved as an historic district, and at the intersection with Harwich Road you can visit the spot where the town first developed in the late 17th century.
Around here you can check out the elegant Brewster Ladies’ Library, built in the Stick style in 1868 and still active.
The road is lined with many of the attractions in this article, as well as a classy roster of antique stores, galleries, hobby shops, home design boutiques, and stately captains’ houses from the 18th and 19th centuries.
4. Cape Cod Rail Trail
This famous, 25.5-mile, rail trail passes through Brewster along the paved railbed of the Old Colony Railroad, which was originally the Cape Cod Central Railroad in the 1860s.
Among the first projects of its kind in America, the Cape Cod Rail Trail came about in the 1970s after the Commonwealth of Massachusetts purchased the right-of-way.
In Brewster it’s a fantastic way to get around by bike or on foot. In the south it runs through a typical Cape Cod landscape of cranberry bogs and ponds.
One of these is Long Pond, the largest freshwater pond on Cape Cod, and the location for Brewster’s public freshwater swimming beach.
The trail runs parallel to the Old King’s Highway for a mile or two before entering Nickerson State Park in the northeast corner.
5. Stony Brook Grist Mill and Museum
There might not be a more idyllic sight on Cape Cod than this historic water-powered grist mill, tucked into a little valley along Stony Brook.
This watercourse was Brewster’s early lifeblood, driving the country’s first ever grist and woolen mill in the late 17th century.
The structure you see at 830 Stony Brook Rd is the last remnant from Factory Village, a commercial community that sprang up at the turn of the 19th century.
The waterwheel and millworks are actually contemporary, and were added in a restoration completed in 2009.
You can come on Saturdays in summer to see the milling process and purchase freshly ground cornmeal.
In spring alewife herring migrate upstream to the millpond to spawn, and this natural event can be witnessed by fish ladders across the road from the mill.
6. Breakwater Beach
The closest public beach to the historic center of town is just a couple of minutes from the Brewster Store and Brewster Ladies’ Library.
Served by two parking lots, Brewster Beach is an enticing stretch of sandy shoreline, walled by low dunes and protected by the namesake breakwaters.
At high tide the beach is rather small and drops quite sharply into the water, which is surprisingly warm at the height of summer.
When the tide retreats, this is another place where you can head out onto Brewster Flats, exploring tide pools or gazing awestruck at the low sun if it’s early or late in the day.
7. Cape Cod Museum of Natural History
If you’re wondering about the Cape’s wildlife, natural history and archeology there’s a family-friendly museum in Brewster next to Stony Brook.
The Cape Cod Museum of Natural History shines a light on a range of topics, from the 10,000 years of human habitation along Stony Brook to the Wampanoag Native Americans, Colonization and early industry.
There’s an aquarium here with more than 80 native species, as well as beehives, a butterfly house and a collection of local bird specimens.
Something else to love about the museum is its outdoor space. There are more than 80 acres on the grounds, but the trails lead into another 320 acres of conservation lands, along the lower reaches of Stony Brook and onto Cape Cod Bay.
There’s a wonderful assortment of habitats to discover including salt marsh, pitch pine woods, beech woods, a barrier beach, and the banks of Stony Brook where you can watch the herring migration in spring.
8. Paine’s Creek Beach
At the mouth of Stony Creek there’s a gorgeous, rock-lined inlet, which is a treat to explore, especially in the summer.
Paine’s Creek Beach is a fun and safe swimming spot when the tide is in, and the ideal place to launch a kayak or stand-up paddleboard.
At these times you can let yourself float from the freshwater creek into the saltwater. At low tide this is another great place to begin an adventure on the Brewster Flats, or simply walk out until you get to some clear water for a swim.
9. Brewster Whitecaps
Cape Cod is famous in the baseball world for the ten-team Cape Cod Baseball League, where future stars of MLB play collegiate summer baseball.
Organized baseball was played on Cape Cod pretty much before anywhere else, and there has been a team in Brewster since the 1880s.
Still, the Brewster Whitecaps are a relatively new creation, entering the league as an expansion team in 1988. A few nascent stars to have turned out for the Whitecaps include Aaron Judge, Jeff McNeil and Kyle Hendricks.
The Whitecaps’ home is the 4,000-capacity Stony Brook Field, opened in 2006 and traced by the Cape Cod Rail Trail. The season lasts from mid-June to mid-August, and Brewster have claimed three championships, in 2000, 2017 and 2021.
10. Drummer Boy Park
A good partner for a trip to the Cape Cod Museum of Natural History is this public park just next door.
Drummer Boy Park comprises an open field with paved trails, benches and mature trees. At the west end stands the Old Higgins Farm Windmill, a smock windmill dating back to 1795 and relocated to its current spot in the 1970s.
Alongside it is The Harris-Black House, from around the same time and thought to be the last surviving primitive one-room house on the Cape.
At the opposite end of the park is a gazebo, serving as the anchor for a series of Sunday concerts and other public outdoor events in the summer.
11. Cape Rep Theatre
This artist-driven theater company in Brewster is based on seven acres of picturesque land at Nickerson State Park.
The Cape Rep Theatre has a quaint indoor space, seating 125 and dating back to 1959 when it was built for a summer camp.
There’s also a lovely outdoor theater for audiences of up to 200 in summer, and this is the only one of its kind on the Cape.
The main season is May through December, during which there’s a wonderful range of productions, from classic Broadway musicals to brand new shows by emerging creative talent.
In the summer there are child-friendly performances during the day, followed by more grown-up fare after sunset.
12. JT’s Seafood Restaurant
Cape Cod has long been known for its clam shacks, which are unfussy window-serve establishments serving New England seafood favorites and other delicious comfort food.
There’s a prime example on the Old King’s Highway in Brewster, at JT’s Seafood Restaurant. Shining lights on the menu are the hot and cold lobster rolls, clam chowder, clam strips, fish & chips, and the lobster bisque.
If you can’t decide, you could always go for a Fisherman’s Platter, with a bit of almost everything. JT’s is also one of a few local spots to pick up some great ice cream, with 20 flavors available, along with fro-yo, soft serve, and sorbet.
13. Crosby Mansion
On the road to Crosby Landing stands a lavish mansion built in 1888 for the entrepreneur Albert Crosby (1823-1906).
After moving to Chicago he made his fortune producing distilled alcohol, which was in high demand during the Civil War. His magnificent 35-room home in Brewster was inspired by the ostentatious residences on Chicago’s Gold Coast.
It was named “Tawasentha” by Albert and his wife Matilda, after Henry Wadsworth Longfellow’s poem. “Song of Hiawatha”.
The construction was on such a large scale that there was even a spur for the property on the Old Colony Railroad during its construction.
Details included a 60-foot viewing tower, extensive hand-carved mahogany fittings, a two-story billiard room, a grand parlor, and a two-story art gallery that had works by the likes of Childe Hassam and El Creco.
The Crosby Mansion still resonates with the opulence of those times, and is open for tours on Sundays in July and August.
14. Harbor Lights Mini Golf
If you’re traveling with kids who want an alternative to Brewster’s history and culture, there’s a classic seaside mini golf course just off the Old King’s Highway.
With its winding paths and abundant grasses, shrubs, flowers and water, Harbor Lights Mini Golf could be mistaken for a garden attraction.
Little boulders are littered across the course, and the main feature is an outcropping with a cave and waterfall.
Skill is rewarded more than luck on these 18 rolling holes. As an extra treat, the course serves Gifford’s Ice Cream, as well as floats, sundaes and shakes.
15. Brewster General Store
A part of local life for more than 150 years, the Brewster General Store is a beloved throwback, selling a bit of everything, and serving as an informal community space with a convivial set of benches in front.
The building is remarkable too, starting out as a church in 1852 before being converted in 1866 when the Cape Cod Central Railroad came through.
The long windows on the side of the building recall the building’s previous role. The likes of Horatio Alger and Helen Keller are known to have visited the store, which owes some of its fame to several generations of vacationers who have called in.
Wares include penny candy, greeting cards, local jams, toys, puzzles, board games, linens, homewares, beach items, books, and tons more.
People stop by early in the day for fresh coffee and pastries, while The Brewster Scoop ice cream stand in the parking lot is another summer essential.