This Small New England Town Is the Perfect Winter Getaway

As a lifelong New Englander, I feel fortunate to experience the beauty of all four seasons. While many dread the cold, long winter months, there’s something special about walking along snowy beaches, cozying up by a fireplace with a festive cocktail in hand, and taking in the Christmas lights wrapped around every streetlamp.

Westerly, Rhode Island, embodies all the best characteristics of a quintessential coastal town: local, family-run businesses, sweeping views of the waves crashing against the jetty, and a rich, deep-rooted history. Originally a maritime hub and a center for granite quarrying, the town has evolved into a seaside tourism destination and continues to welcome visitors year-round.

Although people often prefer to flock to warm-weather destinations when the temperatures turn cold, the quiet yet radiant beauty of winter in Westerly is not to be missed. From sipping hot chocolate with marshmallows to sledding down park hills, there are cozy experiences in every corner of Rhode Island’s westernmost town. Here’s how to plan a trip.

Where to Stay

Ocean House

Ocean House sits atop the bluffs of Watch Hill, a neighborhood with a rich maritime history, and just steps from Taylor Swift’s own “Holiday House,” the home that inspired her song, “The Last Great American Dynasty.” The oceanfront resort offers outstanding hospitality with sophisticated dining, personalized experiences, and wine and culinary arts classes.

Weekapaug Inn

Immersed in nature and surrounded by the Quonochontaug Pond and Atlantic Ocean, Weekapaug Inn blends a love for the water with its luxurious accommodations and modern furnishings. The on-site restaurant sources locally grown ingredients and creates exquisite farm-to-table dining experiences. Nature seekers, make sure to grab a pair of Hunter boots from the Borrowing Closet for wildlife walks and excursions.

Margin Street Inn

Travelers seeking an intimate stay should consider the Margin Street Inn. Nestled along the banks of the Pawcatuck River, the bed-and-breakfast provides European morning fare, including homemade pastries and frittatas, followed by afternoons on the porch with snacks and beverages. The 10 cozy bedrooms, each with a private bathroom, make this a perfect romantic trip or girls getaway.

What to Do

Bundle up for a walk in Watch Hill.

Put on your earmuffs, lace up your boots, and take a stroll past Taylor Swift’s waterfront estate and the Flying Horse Carousel—said to be the oldest operating carousel in the U.S. At the end of the peninsula sits the photo-ready Watch Hill Lighthouse.

Explore the history in the Westerly Downtown Historic District.

Step back into the 19th-century in Westerly Downtown Historic District, where the town’s preserved architecture shows the period’s industrial growth. Across from the library and post office, an adorned Christmas tree sits in Dixon Square, and sparkling wreaths line the streets. There are also boutique clothing shops, a cidery and winery, and inventive restaurants. Around the corner, buckle your ice skates at the community rink.

Immerse yourself in the arts.

With roots going back to 1926, The United Theatre brings culture and arts to Westerly through movies, plays, and live musical performances. With three film venues, the theater creates a uniting space for the community and its visitors, featuring educational and entertainment-based programming.

Where to Eat and Drink

Ella’s Food & Drink

With more than 25 years in the kitchen, James Beard Award-nominated chef Jeanie Roland uses French techniques to create unforgettable dishes at Ella’s Food & Drink. The menu features flavorful dishes like chitara (guitar string) pasta and Momma’s Chicken, best paired an expertly crafted cocktail. From the curry mussels appetizer to chef Jeanie’s famous peanut butter pavlova, you’ll be booking your next reservation before you even leave.

High Hope Tavern

High Hope Tavern, located in the heart of downtown, is a fun cocktail bar and restaurant. Enjoy creative drinks and Rhode Island bounty-inspired dishes, like linguine and clam sauce. Or, go for the iconic Caesar salad and triple-cooked fries served with a delicious garlic aioli.

Nana’s Westerly

Before heading out of town in the morning, stop at Nana’s Westerly for freshly baked sourdoughnuts (sourdough bread made daily with sustainably grown grains) and a hearty breakfast. The Seacoast Mushroom Toast and coconut miso caramel iced latte is a great way to start the day. For lunch and dinner, order pizza made with mold koji, which helps amp up the umami in dishes like the classic Nana’s Tomato.

Perks & Corks

Inventive martinis—don’t miss the dessert-worthy banana split or the famous chai—and cocktails are waiting at Perks & Corks. Guests gather on soft seating around boards of hummus, bowls of soup, and signature grilled cheeses. Pro tip: The bar is the best seat to watch all the magic happen.

Junk & Java

To fully embrace the local coffee scene, head to Junk & Java. Here, you’ll feel the eclectic vibes and energizing staff ready to whip up an iced chai or the customer-favorite Mountain Berry iced tea. Don’t forget to peek next door at the gift shop for funky earrings and locally made artisanal goods.

Where to Shop

Woodmansee’s and Woodees

If you’re looking for a stylish outfit, spend some time playing dress up at these neighboring mother-daughter-run boutiques. Woodmansee’s has styled shoppers for more than 120 years, and Anna, daughter of second-generation owner Maria Lenihan, heads up Woodees, where you can find sparkling holiday dresses and fun statement pieces for cocktail parties or casual outings.

Martin House Books

Get lost in a romance novel or a dark thriller in a cozy corner of Martin House Books. Keep warm with a latte from the in-house coffee shop, Cafe 1888, and stay into the evening for a selection of beer and wine. In the kids area, children can read sitting atop red mushroom stools and peek into the hidden fairy doors scattered throughout the store.

Windie’s

Searching for a fun hostess gift or keepsake? Windie’s specializes in home goods ideal for those who love putting together a Sunday dinner or brunch spread. You’ll spend hours browsing dirty martini-inspired coupes, hand-drawn note cards, tomato-shaped candles, and more.