Rhode Trippin’ to Westerly

The seaside town transforms for Christmastime with shopping, tradition, and no shortage of cheer


Some say that Rhode Islanders don’t like going anywhere more than 10 minutes from home, but with the travel bug biting, many of us are now looking for in-state ideas for an afternoon, daytrip, or staycation. Each month, Bob Curley, author of 100 Things to Do in Rhode Island Before You Die, will share about places to go within our own state border – starting with a road trip to Westerly.


The holiday season may be first and foremost about faith and family, but there’s also a yearning for simpler times woven into our Christmas celebrations and rituals. When I’m in the mood for some real-world Peace on Earth, for example, I enjoy a silent night of walking the streets of Newport, with the windows of its colonial homes lit by flickering candles. But when I’m channeling Dickens — and maybe a little Ralphie Parker — I prefer to bundle up and head down to Westerly.

In normal times, Westerly comes alive during the holidays with a shopping stroll, Santa’s arrival in Dixon Square, and a concert by the Chorus of Westerly. But while things will be different in 2020, even COVID-19 can’t kill the spirit of Christmas.

Santa Claus will still be coming to town, but this year he’ll be greeting kids in a drive-through event at the Ocean Community Chamber of Commerce that will also feature a light display and an outdoor holiday market. “Westerly is committed to maintaining the magic of the holidays and salvaging every time-honored tradition that we can,” says Chamber President Lisa Konicki.

As always, historic Wilcox Park will be open until 9pm nightly so you can wander the manicured grounds of the Victorian-era park to visit the town’s Christmas tree — it’s particularly beautiful with a dusting of snow on the ground. The outdoor Washington Trust Community Skating Rink on Main Street will be open for socially distanced skating all winter long, as well. Hot chocolate is served to keep you warm between laps, or you can pick up coffee at the Savoy Bookstore & Cafe or some hot cider at Perks & Corks, both on High Street.

Downtown’s compact business district is right-sized for holiday gift shopping, with favorites like Christina’s Ltd. and Woodmansee’s gift boutique housed in beautiful brick-faced storefronts reminiscent of an English market town. On the other hand, Westerly’s grand public buildings, including the columned post office and the elegant town library, offer season’s greetings from classic small-town America — perfect for a nostalgic walk on tree-lined streets lit with festive white lights.

As usual, Westerly’s Ocean House — along with its sister hotel the Weekapaug Inn — is going all out for the holidays. The grand Victorian hotel in Watch Hill will raise a Christmas tree of its own on Thanksgiving weekend, kicking off a season of holiday events including classes on making gingerbread houses, Christmas centerpieces, and yule logs.

Kids can have Sunday brunch with Santa at either hotel, and special menus will be offered for a Christmas Eve Feast of the Fishes, along with Christmas Day brunch and dinner. The Weekapaug Inn’s Cinema Under the Stars series will feature holiday movies like Elf, It’s a Wonderful Life, and Miracle on 34th Street.

If ever there was a year to say goodbye to, it’s 2020. The Ocean House sends the old year packing in style with a New Year’s Eve dinner and New Year’s Day brunch, though you’ll have to book a weekend stay to join the party. Feeling hopeful about 2021? Cozy up to a dune at nearby Napatree Point to greet the sunrise on January 1 (or maybe do your own personal polar plunge?), then warm up at the Cooked Goose, one of the state’s top breakfast joints.


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