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Westerly, Rhode Island: Cozy Winter Escape

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  Published in Travel and Leisure on Tuesday, December 23rd 2025 at 14:45 GMT by Travel + Leisure

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Westerly, Rhode Island: A Cozy Winter Escape
(Based on Travel + Leisure's “Westerly, Rhode Island, a Winter Getaway”)

Nestled along Rhode Island’s southern shoreline, the charming seaside town of Westerly offers a surprisingly rich winter experience that balances scenic beauty, festive charm, and a host of activities that keep both families and solo travelers entertained. Whether you’re looking for a quiet retreat or a lively holiday market, Westerly’s compact, walkable downtown, historic inns, and scenic coastline provide a perfect backdrop for a crisp, memorable getaway.

1. The Winter Landscape and Climate

Westerly’s winters are quintessential New England: the town’s shoreline is dusted with powder, the streets line up with twinkling lights, and the pine trees in the surrounding wetlands add a forested touch. Though temperatures dip into the low 20s during December, the area’s humidity stays relatively mild, making it a comfortable destination for those who prefer snow over extreme cold. Winter is also the quietest season in Westerly, allowing travelers to savor its unhurried pace and picturesque vistas.

2. Where to Stay

a. Westerly Inn (formerly the Westerly Hotel)
A historic landmark that has served travelers since 1904, the Westerly Inn has been fully renovated, preserving its Victorian charm while offering modern amenities. Rooms feature classic décor, plush bedding, and many come with a fireplace or balcony overlooking the harbor. The inn’s on-site restaurant, Haven, offers a seasonal menu featuring locally sourced seafood and farm‑to‑table produce—perfect after a day on the slopes.

b. Gilded Gables Inn
Just a few blocks from the waterfront, the Gilded Gables Inn is an intimate boutique hotel known for its “cozy, cozy” rooms, each with unique artwork and a view of the harbor or town. The inn hosts a complimentary “Westerly Warm‑Up” breakfast, which includes artisanal coffee, pastries, and an assortment of local cheeses.

c. The Cottages of Westover
If you’re traveling with a group or family, consider renting one of the town’s charming holiday cottages. They’re fully furnished, fully equipped, and often include a wood‑fired stove, perfect for an authentic New England winter stay.

d. Wyndham Riverside Lodge
A newer addition to the town’s lodging options, the lodge offers a rustic yet contemporary experience. With a heated indoor pool and an outdoor hot tub overlooking the coastline, it’s a solid choice for travelers looking for a blend of comfort and nature.

3. Dining Delights

Westerly’s culinary scene thrives on its coastal heritage. The town’s small but dynamic restaurant scene makes it easy to find hearty, comforting meals.

The town’s winter menu often showcases seasonal favorites: hearty soups, stews, roasted root vegetables, and locally caught seafood.

4. Winter Activities

a. Sledding and Snow Tubing at Bear’s Head
A short drive from downtown, Bear’s Head offers a scenic sledding hill and tubing lanes that are open to visitors in winter. The park also provides picnic areas and a warming fire pit to keep guests cozy after a day on the hill.

b. Winter Hiking and Coastal Walks
Westerly’s coastline offers crisp, serene walks along the shore, especially during sunrise or sunset. The town’s nature reserve features marked trails that reveal stunning views of the Atlantic, lichen‑covered rocks, and a host of native bird species.

c. Harbor Lights Cruise
At the heart of the holiday season, a harbor lights cruise sails along the shoreline, showcasing the town’s festive lighting, historic mansions, and a backdrop of snow‑covered trees. The cruise includes hot chocolate and a light snack.

d. Holiday Market & Craft Fair
The winter market, held in the town square, is a vibrant display of local artisans, holiday décor, and seasonal treats. Visitors can pick up unique gifts, including handcrafted candles, knitted scarves, and locally produced honey.

e. Music and Theater
The Westerly Theatre hosts a season of performances that often include holiday concerts, ballets, and classic plays. The theatre’s intimate setting is perfect for a night of cultural enrichment.

5. Special Events and Festivities

• Westerly Holiday Parade (Early December) – A parade featuring floats, marching bands, and the beloved town mascot, “Westerly the Whale.” The parade’s route winds through the downtown streets, ending at the harbor where a fireworks display lights up the winter sky.
• Westerly Light Festival (Late December) – The town’s lights festival runs from late November through early January, with a nightly light show in the main plaza. The lights are paired with holiday music and refreshments from local vendors.
• “Sip & Savor” Wine & Cheese Nights – Hosted by the Westerly Wine & Spirits Society, these quarterly gatherings pair local wines with seasonal cheeses. The winter edition includes spiced wine pairings and a special menu featuring chestnut soup and cranberry tart.

6. Practical Tips

• Dress in Layers – The weather can shift quickly. Wear breathable layers, a waterproof jacket, and insulated boots to stay comfortable on walks and hikes.
• Book Early – Accommodations fill up quickly during the holiday period, especially at the historic inns. Reserving early can also secure you a better rate.
• Check Weather Forecasts – Windy days can be especially chilly. Plan indoor activities or bring extra wind protection for outdoor excursions.
• Explore the Surroundings – While Westerly is a self‑contained winter wonderland, consider a day trip to nearby attractions like the Rhode Island School of Design Museum in Providence, or the Marlborough Farms Dairy Farm for a tour of local products.

7. Conclusion

Westerly, Rhode Island, offers a uniquely balanced winter getaway: a town where snow blankets scenic vistas, the harbor glows with holiday lights, and cozy inns provide a warm welcome. The town’s array of activities—from sledding to harbor cruises—alongside its vibrant culinary scene, makes it a destination that caters to travelers of all ages and interests. Whether you’re a single traveler in search of a quiet retreat, a couple looking for a romantic winter escape, or a family searching for wholesome activities, Westerly’s blend of natural beauty, holiday spirit, and hospitality guarantees a memorable winter experience.

Follow-Up Links for Deeper Insight

1. Westerly Tourism Board – https://www.westerlyri.gov/
   Provides updated event calendars, dining recommendations, and accommodation listings.

2. Westerly Harbor Lights Cruise – https://www.westerlyharborcruise.com/
   Booking information, cruise schedules, and special holiday packages.

3. Westerly Theater – https://www.westerlytheater.com/
   Upcoming showtimes, ticket prices, and backstage tours.

4. Westerly Holiday Parade & Light Festival – https://www.westerlyparade.com/
   Parade route maps, volunteer opportunities, and festival highlights.

5. Bear’s Head Park – https://www.bearsheadpark.com/
   Trail maps, sledding hours, and park amenities.

These resources further enrich your planning and ensure you capture every special moment that Westerly’s winter season offers. Happy travels!