Westerly, R.I., is an often-overlooked stop on the I-95 corridor, but just a few miles off the highway, this town has so much to offer. Downtown Westerly is having a cultural renaissance: Old buildings, once in disrepair, are being redeveloped into everything from a bookstore that serves wine to a pinball arcade to a multi-use theater that will host innovative educational programming and major shows when it opens next year.
Start your trip off with the most important meal of the day, at the best place in town to have it. The Cooked Goose serves New England breakfast – don’t miss the lobster eggs Benedict with lemon tarragon hollandaise – and prepared foods to go, so you can stock up on provisions and take them with you to the beach.
The sandy stretch of Westerly, R.I., called Misquamicut is home to several beaches, where you can rent a personal watercraft, ride a wave or just catch some rays. It’s also one of the only places in Rhode Island with honest-to-goodness beach restaurants where you can walk right inside in your bathing suit. Head to The Windjammer Surf Bar or The Andrea if you’re looking for a festive atmosphere with live music and perfectly summery frozen drinks. Atlantic Beach Park has kids’ rides and arcade games, and you’ll find waterslides galore at Water Wizz.
If you’re lucky enough to be in town for one of the summer’s Shakespeare in the Park performances, make sure you bring lawn chairs and a picnic basket. The Colonial Theatre is staging “A Midsummer Night’s Dream” in July and August in Wilcox Park, a beautifully landscaped space with sculptures, gardens and ponds. Nearby, The Knickerbocker Music Center, which has been hosting musicians since 1933, has live music five nights a week. Grey Sail Brewing is a tasting room with rotating selections, including its signature Flying Jenny American pale ale. It’s only open until 8 p.m., but just down the street, The Malted Barley has 38 beers on tap, many of which are local, and gourmet soft pretzels to go with them.
As far as Westerly hotels go, you can’t do better than Ocean House, Rhode Island’s only AAA Five Diamond Rated hotel. (It’s also home to the state’s only Five Diamond Rated restaurant, COAST, which has a farm-to-table tasting menu that changes nightly). Even off-season, the luxury Watch Hill resort can be pricey. But with panoramic views of Block Island, Shelter Island and Taylor Swift’s house just down the street – plus a private beach, on-site spa, boat rides and sports car test drives – the splurge is worth it. Its sister property, the more casual Weekapaug Inn features an in-house naturalist who will take you on tide pool explorations and kayak excursions.
Start your Sunday at the Savoy Bookshop & Cafe, which serves locally roasted coffee and muffins fresh from the oven, with plenty of comfortable seating for you to linger over the Sunday papers. Don’t fill up on carbs, though. The Sunday Jazz Brunch at Ocean House is not to be missed. This isn’t your average buffet: raw bar, charcuterie shaved to order, freshly made crepes and an entire table of desserts will have you loosening your belt, while the bottomless Champagne will help you wash it all down.
Explore the rest of the Watch Hill area by foot. There are lots of small shops that are worth a look, and the country’s oldest operational flying horses carousel. The long stretch of beach at Napatree Point is perfect for a nature walk. The Napatree Point Conservation Area is a nesting ground for migrating birds, and because there are no vehicles that far out on the sand, it’s a serene place to clear your head and watch the boats sail by. On the opposite side of Watch Hill is the Watch Hill Lighthouse, with a small museum devoted to the area’s seafaring history. (If you’d rather hike away from the sand, The Westerly Land Trust has a wealth of guided and self-guided routes through the town’s scenery.)
Even if you’ve had your fill of Westerly restaurants, head to the Weekapaug Inn before you go. The lawn has Adirondack chairs perfectly positioned to watch the sunset (with or without a glass of wine, depending on who’s driving) and the inn lights up the fire pit for s’mores as soon as dusk sets in. Before you head home, make a stop at Sandy’s Fine Food Emporium and pick up some soupy to take back with you. The signature food of Westerly, soupy is a local take on soppressata that evolved from Italian families making the dry-cured sausage at home. It’s spicy and delicious, and will serve as a nice reminder of your weekend once you get home.
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