America’s Most Charming Holiday Small Towns

The festive fun awaits

‘Tis the season—for traveling, that is! The holidays are one of the most magical times of the year to get away. Twinkling lights, decorated downtowns, and cocoa-fueled strolls make everything feel merry and bright. And what better way to lean into the season than by exploring charming holiday small towns that go big on holiday spirit?

Pack your cozy favorites, cue your holiday playlist, and soak up the holiday cheer at these festive destinations.

• Franklin, TN

  For that classic holiday vibe!

  Franklin truly turns on the charm during the holiday season. Its historic Main Street is brimming with red-bowed garlands, wreaths, and vintage-inspired lamppost decorations. Be sure to peek at the elaborate window displays, a Franklin tradition!

  One of the best ways to see the town’s holiday cheer is aboard the trolley, on the Holiday Lights Tour. For almost two hours, you’ll listen to holiday music, snack on candy canes, and take in the town’s stunning displays.

  But what truly makes Franklin one of the country’s most charming holiday small towns is its signature event, Dickens of a Christmas. Downtown Franklin transforms into a Victorian village, complete with performers, carolers, handcrafted goods, and costumed characters. Keep your eyes open for Scrooge!

• Leavenworth, WA

  Holidays with an alpine flavor!

  A trip to Leavenworth feels like you’re in Europe, without a passport. Think Bavarian architecture, German food and drinks, and a legendary Oktoberfest celebration. And the alpine fun gets a seasonal makeover during the holiday season. Stroll through the traditional Christkindlmarkt for European-inspired treats, artisan crafts, spiced wine, and Bavarian-style performances.

  The season kicks off with the Village of Lights, which starts on Thanksgiving night. The town glows with over half a million lights, plus live music, strolling carolers, kids’ crafts, hot cocoa stations, and photos with Santa himself.

  Even Leavenworth’s outdoor life takes on an alpine touch. The snowy landscape offers sledding hills, cross-country ski trails, and snowshoe paths along the river. Warm up afterwards with hot spiced wine.

• St. Augustine, FL

  Looking for a warm winter escape?

  One of our favorite holiday small towns trades snow for sand. St. Augustine brings a warm, coastal twist to the holidays—and one of the most impressive light displays in the country. The city’s long-running Nights of Lights covers historic buildings, palm trees, and waterfront paths with millions of white bulbs.

  The historic district brings its own holiday charm. Sing-along trolley tours stop at holiday stations, while boat tours offer illuminated views. Even iconic landmarks like the Bridge of Lions get a festive display! Feeling loved up? Take a carriage ride through cobblestone streets and along the bayfront for a romantically festive date night.

  Food is part of the holiday fun, too. Outdoor patios serve coastal holiday favorites, from fresh seafood to specialty themed cocktails.

• Woodstock, VT

  A picture-perfect holiday destination!

  Woodstock feels like it was just made for the holidays, you guys. It has the quintessential New England appeal, from snowy streets to bright wreaths and a village green. In Woodstock Village, shops offer gifts and treats created by local artisans, while windows glow with garlands and twinkling lights.

  Woodstock leans even further into the season with its famous Wassail Weekend. The town’s most popular celebration includes horse-drawn carriage rides and a festive parade inspired by 19th-century traditions. Ornament workshops, garland making, hot chocolate, and an artisan market on the Historic Village Green round out the seasonal festivities.

  Woodstock is also ideal for outdoor wintry fun, with snow-dusted trails perfect for cold-weather hikes among the evergreens. A fireside meal or hot cider in a cozy inn will warm you up afterwards.

The country’s most charming holiday small towns offer everything you need for a festive getaway filled with pure December magic.

And to make sure you arrive feeling merry and bright, ship your bags to your holiday destination with LugLess. No hauling bags through the airport, and no feeling like the Grinch at baggage claim. Just you, your Ugly Christmas Sweater, and alllll the holiday cheer!