21 Romantic Things to Do in Brewster MA: On Cape Cod

WHY GO: With an abundance of things to do in Brewster MA, and plenty of romantic places to stay nearby – from mega resort to old fashioned inn to intimate B&B – it makes sense to stick around this mid-Cape town for a few days, especially if you’re with a special someone.

Brewster makes for the perfect base to access the Cape Cod Rail Trail. The closest Whale Watching cruises leave from Orleans, just a 15 minute drive. But other than that, what to do? Where to bed down?

There are so many places to stay while visiting Brewster, it can get confusing. We unpack all the attractions, restaurants, and lodgings below so you can choose wisely.

If you wish, use this post to continue on your Cape Cod Route 6A journey.

Things to Do in Brewster MA

Cape Cod Museum of Natural History Dennis MA

VISIT: Cape Cod Museum of Natural History

Visit the Cape Cod Museum of Natural History to hike on trails through wildflower gardens, meadows, over creeks, on dunes, beaches and mudflats. Head upstairs to an eye-catching Salt Marsh exhibit in a solarium with panoramic views of wildlife-rich wetlands.

Downstairs, you’ll find the low-keyed type of aquarium that, as a child, used to absorb you for hours: tanks full of fish, turtles, snakes and other local shoreline creatures.  You might just come across a few with engaging personalities.


Founded in 1986, the Cape Rep Theater, on the fringes of Nickerson State Park, offers lesser known and new productions in both a 135-seat indoor theater, and in Cape Cod’s only outdoor theater, (seating 200). For seasonal and even first time visitors, one of the primary things to do in Brewster MA in the summer months is to snag a seat there: especially when The Rep is staging a world premier.

Brewster Store on Cape Cod MA

SHOP: Brewster Store, Brewster

Stop to stomp on the old wide-planked floors of The Brewster Store, an old fashioned General Store of Yore (though the prices here are decidedly modern).  Baskets of tchotchkes, a jumble of stuff, you could browse around for hours.

Cobalt glass, lobster magnets, fudge, and those candy sticks forever associated with elementary school field trips can be found among suspenders, mood rings, antique tin signs and a bazillion other things on two floors.

SHOP: Sydenstricker Glass

All the unique suncatchers, luncheon plates, and other glassware sold in the modest Sydenstricker Glass on Route 6a is hand-made in this very shop. Some designs have ended up in galleries and museums (including Museum of Modern Art in NYC). So, it’s quite refreshing to find that prices are reasonable.

PHOTO OP: Stony Brook Grist Mill and Museum, Brewster

What draws us to water wheels? Especially those that turned grains to flour back in the 1700’s – 1800’s?  Perhaps we’re in awe of the technology dreamed up by engineers of the day.The Stony Brook Grist Mill is the last remnant of Brewster’s 19th century industrial past.  These days, see how the waterwheel worked and how flour was milled without computers or even electricity.

STOP: Brewster Ladies Library

Of all the things to do in Brewster Massachusetts, this might be the oddest. Why would a library open for women only? Well, it has everything to do with the date that the Brewster Ladies Library was established – 1852 – when women were still second class citizens. In fact, 1852 was the very year that Susan B Anthony began protesting for women’s rights.

That year, a dozen local sea captains wives felt the need for all women to have access to information and knowledge. That the town of Brewster kept the name of the library all of these years is testament to that rebellious history.

Brewster MA Breakwater Beach

BEACH: Breakwater Beach – Salt Water

Off season, you just might have Breakwater Beach to yourself.

Point of Rocks Landing Beach Cape Cod

BEACH: Point of Rocks Landing – Salt Water

Due to lack of parking, it’s best to bike through tidy neighborhoods to Point of Rocks Landing. You’ll be sharing sand space with residents lucky enough to have this sandy beach right in their backyards.

BEACH: Long Pond Brewster Beach – Fresh Water

You won’t find any prickly salt water (or sharks, for that matter), in Cape Cod’s largest freshwater pond. Long Pond is so long, it stretches from Harwich to Brewster. Practice your breaststroke in a marked off area at Long Pond’s Brewster Beach – there’s even a floating dock for swimmers.

PUTT PUTT: Harbor Lights Mini Golf – One of the Best Date Night Things To Do in Brewster mA

What’s a summer vacation spot without mini golf? This one’s got several cool water features, including a waterfall, and is oh so romantic on a sultry summer night. Pair it with a scoop of freshly made ice-cream (see below) for a classic beach town date night.

ICE CREAM: Brewster Scoop

Brewster Scoop – near the Brewster General Store – has been satisfying summer sweet tooth’s for decades. Grab a cone and head to Harbor Lights Mini Golf. I’ve heard the stuff improves your swing!

Best Restaurants in Brewster MA

Cobies Clam Shack Cape Cod MA

SNACK; Cobie’s Clam Shack, Brewster

Cobie’s is a picture-book roadside stand that serves up ice-cream, golden fried clams, hot dogs and all the great paper-plate dishes of summer. Burgers, Lobster Roll, Box of Fried Clams – no frills, pure summer-shack ambiance.

EAT: Chillingsworth Restaurant and Chills Bistro, Brewster

If you’re feeling flush or are celebrating a special event, plan an evening at the excellent Chillingsworth Restaurant and Chills Bistro. Zagat’s deemed Chillingsworth “worth the drive from anywhere.”

If you want to rush or catch a movie, ask to be seated in the Bistro – a more causal and lower priced section of the restaurant. For a meal to savor, reserve a table one of the intimate dining rooms in a gracious circa 1600’s home.

JT's Restaurant Brewster MA

EAT: JT’s Seafood Restaurant

If your taste buds crave a hot lobster roll or cold ice-cream cone, pop on over to JT’s. You’ll find all manner of Cape Cod’s summer cuisine, including Clam Strip Rolls, oysters – and other “snack bar” items – at this nothing fancy, but good eatin’ casual spot.

Brewster Fish House Cape Cod MA

EAT: Brewster Fish House

Inclined towards more of a fine-dining experience? Good news! It’s first come first served (no reservations taken) at Brewster Fish House, a sensation of a restaurant.  Some of the most innovative, contemporary dishes emerge from the kitchen in this cozy cottage right on Route 6A.

Where to Stay in Brewster MA

Ocean Edge Resort Cape Cod Mansion Side Brewster MA

STAY: Ocean Edge Resort and Golf Club

The Ocean Edge Resort combines the best elements of a sports club, golf club, social club, beach club, high-end hotel, and top notch dining in one place, allowing you to live like a happy upper-crust Victorian. For as long as you stay. A Maven Favorite, we wrote up the Ocean Edge Resort Review on its own page.

Candleberry Inn Brewster MA

STAY: Candleberry Inn, Brewster

In new hands for several years, The Candleberry Inn has been updated to Select Registry standards. As such it’s a Maven Favorite – with a complete write-up and review in this Candleberry Inn Post. 

STAY: Captain Freeman Inn, Brewster

The Captain Freeman inn is first choice of many discerning Cape Cod bound travelers.  After purchasing Captain Freeman a few years ago, Laurie & Jason Stuehmer renovated “every inch of the inn”: creating a calm, elegant, and lovely oasis. “Guests are pampered from the minute they arrive,” says Laurie.

Old Sea Pines Inn Brewster MA

STAY: Old Sea Pines Inn, Brewster

Steve and Michele Rowan have kept a “resort of a former era” vibe alive at this former elite boarding “Charm School” for young women, now a 24-room inn. Burnished wooden floorboards, floral quilts on the brass beds – each room is unique, fresh and lovely.

Old Sea Pines is not on the beach.  It is not high tech or flashy. There are no TV’s in the rooms.  “It is what it is, and we want it that way,” Michele says.

Best bet for a lazy early evening; enjoy a glass of wine or a beer while settling into a rocking chair on the sheltered front porch.This place is a rare find; a “resort” location at reasonable rates.

CAMP OUT: Nickerson State Park

If your idea of a romantic getaway is in a tent on the oceanfront property (or at least nearby), Nickerson State Park delivers. For just $22 (in-staters), or $70 (out of staters), you can get one of the best campsites on Cape Cod and the Islands.

Weekend Getaways In Cape Cod (And Nearby)

Want wilder vibes? Head to Provincetown at the tip of The Cape

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  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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