There’s a version of the holidays that doesn’t involve a crowded mall or a maxed-out to-do list, and you’ll find it on the Connecticut shoreline in December. Historic towns strung with lights, boat parades on the river, and a coastal inn with a fireplace waiting at the end of the day. This is what a slower, more charming holiday season looks like. Here’s a 48-hour December itinerary based out of The Captain Stannard Inn in Westbrook, CT.
Day One: Arrival and a Cozy Start
Check into The Captain Stannard Inn, where the fireplace lounge and Portside deck take on a whole new mood once the temperature drops. This 1872 sea captain’s house was built for exactly this kind of evening. Settle in, warm up, and let the coastal-farmhouse decor do its quiet holiday work without a single plastic reindeer in sight.
For dinner your first night, stay close to home. Westbrook’s small-town Main Street has cozy dinner spots perfect for a cold night, many decorated for the season and well suited to a slow, unhurried meal before you head back to the inn.
Day Two Morning: Old Saybrook Torchlight Parade Season
If your visit lines up with mid-December, don’t miss the Old Saybrook Torchlight Parade, a shoreline holiday tradition where more than twenty fife and drum corps march down Main Street to the town green, led by the 2nd Company Governor’s Foot Guard. It’s a genuinely old-school New England holiday event, ten minutes from the inn, and worth building your whole trip around if the dates align.
Afterward, warm up with coffee and breakfast pastries from a local Old Saybrook café before heading out for the rest of the day.
Day Two Afternoon: Boat Parades and River Towns
Drive twenty-five minutes north to Essex for the Trees in the Rigging Boat Parade, a genuinely unique Connecticut shoreline tradition where boats decked out in holiday lights cruise the Connecticut River. Pair it with a visit to the Essex Steam Train’s holiday season, which runs seasonal excursions along the river through December. Check current-year dates and ticket availability before you go, since these sell out fast.
While you’re in the area, wander Essex’s small downtown for holiday shopping at independent shops. It’s the kind of walkable, string-lights-overhead town that makes for good afternoon photos and better gift finds than anything at a mall.
If your December visit falls earlier in the month, the Stonington Lobster Trap Tree, built from hundreds of lobster traps and buoys painted by shoreline kids and adults, is worth the slightly longer drive east. It’s become one of the most photographed holiday landmarks on the entire Connecticut coast.
Day Two Evening: Dinner, Lights, and a Quiet Night
Head back toward Westbrook for dinner. This is a good night for a warm, hearty meal at one of the shoreline’s seafood or Italian spots. Dattilo Italian Steakhouse at Water’s Edge Resort is a strong pick for a cold-weather dinner with water views, even in December.
Before heading back to the inn, take a slow drive or walk through Westbrook’s own Main Street to see the town’s holiday lights. It’s a smaller, quieter display than the bigger river towns, but that’s exactly the appeal: no crowds, no lines, just a genuinely festive small town doing its own thing.
Back at The Captain Stannard Inn, close out the night by the fireplace. This is the entire reason to choose a historic inn over a chain hotel in December: a common space that actually feels like someone’s living room, decorated for the season, with nowhere else you need to be.
Day Three: Slow Morning Before You Go
Wake up to breakfast at the inn and take one more walk toward the beach. Long Island Sound in December has its own stark, beautiful quiet. Head home with a trunk full of local gifts and a phone full of boat-light photos.
Why the CT Shoreline Does the Holidays Right
The Connecticut shoreline in December skips the commercialized chaos and leans into what small New England towns actually do best: parades with actual marching bands, boats strung with lights instead of a mall Santa, and towns small enough to walk end to end. Basing your trip at The Captain Stannard Inn puts you within a short drive of every major holiday event on the shoreline, Old Saybrook, Essex, and beyond, while giving you a genuinely warm, historic place to land each night.
Book your December stay at The Captain Stannard Inn and let the Connecticut shoreline’s holiday season do the rest.
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