15 Best Things to Do in Westport (MA)

This archetypal New England seaside town is at the western edge of Buzzards Bay, right against the Massachusetts/Rhode Island border.

Westport’s shore is full of drama, where the marvelous Horseneck Beach unrolls for two miles, skirted by dunes.

At the eastern end of the beach is Gooseberry Island, jutting out into Buzzards bay for stupendous ocean views.

Inland, Westport is all pastoral farmland, criss-crossed by stone walls and scattered with centuries-old houses, a mill operating since the 17th century, a celebrated winery, contemporary art galleries, and reservations for gentle country walks.

1. Horseneck Beach State Reservation

A place of raw natural beauty, this 800-acre public recreation area features two miles of sandy barrier beach, dunes, marshland and a sheltered estuarine habitat.

Horseneck Beach State Reservation attracts hundreds of thousands of people every summer, with lifeguards on duty July 1 through Labor day.

The beach faces southwest on a sandy crescent bathed by low, rolling waves, and naturally strewn with cobblestones, so pack water shoes if you plan to wade in the shallows here.

There’s a campground at the east end of the beach by Gooseberry Neck, with 100 sites, each one equipped with a fire ring and picnic table.

2. Allens Pond Wildlife Sanctuary

East of Horseneck Beach is the ecologically rich Allens Pond Wildlife Sanctuary, protecting a tapestry of habitats, on the shore and inland.

On more than 600 acres, along seven miles of trails you can venture over or past a beach (1.5 miles long), woodlands, Allens Pond, marshes and agricultural fields with maze-like stone walls.

On your travels you’ll come to many vantage points for observing the sanctuary’s diverse wildlife, with more than 300 bird species recorded on this property.

One significant resident is the piping plover, which nests on the beach in the summer. There’s a schedule of wildlife-oriented programs at the quaint Stone Barn, built in the mid-19th century, and on a sunny day in summer the butterfly garden is a delight.

3. Gooseberry Island

Linked to the mainland by a short causeway, the solitary Gooseberry Island is at the southern tip of Horseneck Beach State Reservation.

Buffeted by ocean winds, you can easily spend an hour or two exploring the island via the looping sandy path, pausing every now and then to marvel at panoramas of Buzzards Bay.

This place has been recognized as a lookout for a long time, and during WWII became the logical position for a concrete observation tower, still in situ, to spot German U-boats.

The west side is windswept, with waves crashing against the rocky shoreline, while the east side is sheltered, with a sandy beach lapped by gentler surf.

4. Osprey Sea & Surf Adventures

One of the best things you can do in summer in Westport is taking a paddling trip along the town’s safe waterways.

To help you, this store is right on the navigable East Branch of the Westport River, selling and renting all you could need for kayaking, canoeing and stand-up paddleboarding experiences.

The location is the perfect launching spot, with no need for road transfers. Osprey Sea & Surf Adventures is busy all summer long, organizing camps, tours and lessons, teaching important paddling techniques, vessel control and safety.

5. Handy House

Owned by the Westport Historical Society, the Colonial Handy House is a unique showcase for architectural trends in southern Massachusetts in the 18th and early 19th century.

Beginning with the three bays on the right hand (east) side, the house was built in three distinct stages between around 1710 and 1825, when it reached eight bays.

The interior has been left sparsely furnished, so you can easily detect the different phases of construction, getting a close look at the walls, plaster work, floors, hinges, windows and other architectural elements. The Handy House is normally open on Saturdays during the summer.

6. Gray’s Grist Mill

By the state line on Adamsville Rd you’ll be greeted by a scene that looks like something out of a picture book.

The shore of Gray’s Mill Pond, dating back to the 17th century, is hemmed by quaint old buildings, one being this water-powered grist mill. With enormous 54-inch granite stones, this mill has been grinding corn continuously for more than 360 years.

Today, Gray’s Grist Mill’s cornmeal comes from local Rhode Island Narragansett Flint Corn, which is matured in open-air corn cribs by the elements.

At the store you can buy special mixes for jonnycakes and pancakes/waffles, as well as Rhode Island maple syrup, local roasted coffee and recipe books.

7. Buzzards Bay Brewing

You’ll never have to search long for a craft brewery in Massachusetts, but there aren’t many with a reputation as strong as Buzzards Bay Brewing.

This can be found on a farm in pastoral fields bounded by woods, and using locally grown/made ingredients, including the farm’s own wheat.

Two of the star brews are Flounder, an unfiltered Blond Ale made with a blend of white wheat malts and local barley.

Buzzards Bay IPA meanwhile is more than just another IPA, as it’s made with a new crop of hops each year, creating new aromas and flavors.

There are more than a dozen other beers in the regular rotation, as you’ll discover at the taproom, which is homey in winter and has ample outdoor space in the warmer months.

8. Portas Da Cidade

Southeastern Massachusetts has had significant Portuguese heritage since the late 19th century following immigration from the Azores and Madeira.

This is still noticeable in things like cultural celebrations, churches, but also the food, so you’re in a good place to try some authentic Portuguese dishes with recipes that have been passed down generations.

That is true of Portas Da Cidade, which in real Portuguese style has a range of codfish (bacalhau), breaded, stewed, grilled, or baked.

Some popular choices are the Mozambique-style shrimp, the grilled sirloin with stuffed shrimp, and the classic Bife á Portuguesa, a sirloin topped with egg in a rich sauce.

9. The Bayside Restaurant

Near Westport Point, this family-owned and operated restaurant has a sensational view, taking in Buzzards Bay, the Elizabeth Islands, and a swath of Allens Pond Sanctuary.

The Bayside Restaurant’s specialty is New England-style seafood, fresh from the Atlantic and sourced from New Bedford and the Boston waterfront.

Think lobster rolls, fried scallops, fried clams, and fish & chips. Many of the recipes have been in the family for generations, and this goes for the selection of delicious house-baked pies, from lemon to apple, blueberry and meringue.

10. Westport Town Farm

Sloping down to the East Branch of the Westport river, this 40-acre preserve is managed by the Trustees of Reservation, and has a compelling story to tell. For more than a century the property was Westport’s poor farm and infirmary.

A farmhouse, barn, corn crib and Colonial stone walls all speak to the age of this site. Beginning at the barnyard you can traverse a landscape of hillside pastures, hay meadows and paddocks framed by old stone walls.

On the mile-long loop you’ll be able to look out over the tidal river and its salt marsh, before circling back up to the barnyard.

11. Camara Conservation Area

The Westport Land Conservation Trust takes care of a number of smallish natural spaces around the town, and one to keep in mind is this 43-acre parcel of mixed hardwood forest and freshwater on the expansive South Watuppa Pond.

There’s a half a mile of trails on the property for a brief intermission during the day, with a spur leading you north to a large glacial erratic.

The Camara Conservation Area is in an area with ample public open space, crossing into Fall River, and the town of Tiverton, Rhode Island.

12. Dedee Shattuck Gallery

Named for its owner, this contemporary art gallery is in a bucolic patch of forest and meadows, in a building that takes its cues from Westport’s historic Quaker architecture.

A cultural destination for Westport, the gallery is a platform for a constantly growing roll call of emerging local artists, but also noted regional, national and international names.

Open April through December, the Dedee Shattuck Gallery presents engaging solo and group exhibitions, and has an exciting schedule of events, with live performance, readings, talks, and discussions.

13. Westport Rivers Vineyard & Winery

Planted in 1982 and opened in 1986, this vineyard is run by a family with four generations of winemaking heritage.

This beautiful parcel of land was chosen for its well-drained, dark New England loam soils, and for the climate in Southeastern Massachusetts, which is cool, but tempered by the Gulf Stream.

Mirroring famous regions like Burgundy and Champagne, Westport Rivers uses traditional methods, with minimal processing, to craft varietal wines like Riesling, Chardonnay, Pinot Noir, Pinot Gris, and Grüner Veltliner, as well as a choice of sparkling wines.

The winery is open for tours and tastings, Monday to Saturday, and always has something fun happening, with a sunset concert series in summer, and vineyard hayrides in fall.

14. Weatherlow Farms

Established in 2014, Weatherlow Farms raises grass-fed meat (beef, lamb, chevon, pork), along with pastured poultry and eggs.

Another forte is flowers for special events, grown and curated on the farm, while the elegant post-and-beam barn on the property is a venue for weddings, parties and other private functions.

If you’re just passing by you can call in at the farm store at 845 Sodom Rd, that high-quality meat and poultry, as well as flowers, plants, baked goods, dairy items, homemade sauces, pickles, frozen prepared foods and even pet treats.

15. Gray’s General Store

Just a few feet from the Gray’s Grist Mill in Adamsville, Rhode Island, you’ll come across a rustic-looking building with a sign reading Gray’s on the porch.

This was believed to be the oldest continuously operating general store in the United States, open from 1788 until closing in 2012 when its owner Grayton Waite passed away.

He had been the sixth generation to run the store, which reopened in 2013 when his son and sole heir rented the property to his father’s cousin, who had worked here for 16 years.

In the early 19th century this building also contained the village of Little Compton’s first post office. Gray’s General Store sells collectibles, gifts, antiques, frozen treats, bagged candy and more.