There’s nothing like being home for the holidays—but there’s certainly something to be said about getting away in the days leading up to the holidays. Whether you’re desperately searching for your inner holly-jolly or you’re already decked out in head-to-toe tinsel and chugging a peppermint latte 24/7, there’s no better way to get in the holiday spirit than with a yuletide visit to one of these quintessential New England towns.
Woodstock, Vermont
Woodstock is worth a visit any time of the year, but the holidays are when the town truly shines (literally).
Don’t Miss: Wassail Weekend, held December 12–14 this year, is the pinnacle of holiday fun, with historic homes decorated in full holiday regalia, twinkling light displays, horse-drawn carriage rides through town, Victorian-themed celebrations, open-air holiday markets, adult beverages, live music, a parade, and more.
but also: Even if you don’t make it to Wassail Weekend, the entire holiday season in Woodstock offers a tapestry of festive activities. Shopping for unique Vermont gifts, arts and crafts, fine jewelry, and more is always on the table, and from December 20–January 4, you can travel to Christmases past with firepits, hot cocoa, cider doughnuts, farm animal meet-and-greets, a bedecked farmhouse, and outdoor activities like snowshoeing at Billings Farm & Museum.
stay awhile: The centrally located and pet-friendly Woodstock Inn & Resort boasts an onsite spa, four distinct restaurants serving farm-driven cuisine and innovative cocktails, Nordic skiing trails, an indoor pool, and sumptuous accommodations that honor the Inn’s connection to Laurance Rockefeller.
Freeport, Maine
Freeport offers 37 miles of tidal coastline, inspiring galleries, more than 3,000 acres of preserved land for outdoor fun, craft beer, and outlet shopping galore.
Don’t Miss: The Sparkle Celebration has become one of Maine’s signature annual events, and this year’s festivities kick off on December 5 with a Parade of Lights. The evening concludes with Santa arriving just in time to animate the talking Christmas tree, and the celebration continues through the 14th.
but also: Once you’ve chatted with enough elves and gotten your fill of hot cocoa, you’ll want to stock up on gifts at L.L. Bean’s flagship store (open 24 hours a day, 365 days a year), grab deals at outlet stores (like Ralph Lauren and Patagonia), and peruse some of Freeport’s top boutique apparel stores (check out Rustic Arrow for new additions to your winter wardrobe and Wilbur’s of Maine Chocolate Confections to satisfy your sweet tooth).
stay awhile: The historic Harraseeket Inn feels like a destination unto itself, but it’s just a heartbeat away from downtown. There are 90-plus rooms, suites, and townhouses to choose from, plus an indoor pool and an onsite restaurant that showcases locally grown fare with global inspiration. It’s all well within walking distance of the town’s many shops, galleries, watering holes, and restaurants.
Stockbridge, Massachusetts
Nestled in the Berkshires, Stockbridge is known for many things, including top-notch cultural attractions that rival sophisticated urban centers, stunning trails for skiing and snowshoeing, historic homes, and—oh, yeah—a classic New England holiday festival.
Don’t Miss: Stockbridge Main Street at Christmas formally runs December 6–7, though its impact spills out on both ends of the action-packed weekend. The fun begins with a Historic Holiday Property Tour, followed by a holiday concert and group sing-along on Saturday. And on Sunday, the main event: Main Street is transformed into what Norman Rockwell saw when he painted the iconic work for which the holiday celebration is named. There’ll be antique cars parked, festive activities, Victorian Carolers, food, and seasonal beverages.
but also: Can’t get there that weekend? The joyful air of holiday cheer remains through the holidays; you’ll definitely want to visit the Norman Rockwell Museum, check out one of the many studios and galleries, or get an adult beverage at Berkshire Mountain Distillers.
stay awhile: The Red Lion Inn offers rooms at the historic inn itself, plus guest cottage stays. And then there’s the inn’s self-guided art and history tours, seasonal live music events, heated outdoor pool and hot tub, spa, and one-off special events like magic shows and murder mystery weekends. Make sure to check out the afternoon tea service, and later, the Lion’s Den, a speakeasy under the inn with classic pub fare, local brews and hand-crafted cocktails. The inn also has a floristry and home boutique store as well as a shop with jewelry and accouterments for the home.
