25 Festive Christmas Towns to Visit for the Holidays

A combination of luxe living and quaint charm helped this Rocky Mountain town become one of the merriest in the country. Wandering along Cooper Avenue, you may chance upon cookie exchanges, public s'mores roasts, or elf meet-and-greets. The 12 Days of Aspen celebration happens from Dec. 20 to 31 this year — for a full list of activities, visit the Aspen Chamber calendar. And don't miss the three most famous hotels in town while you're here for the holidays. The lobby of the Hotel Jerome, Auberge Resorts Collection often hosts carolers, while the Ajax Tavern and Element 47 at the Little Nell both serve fabulous holiday meals. Looking for a bird's-eye view of the decorations? You can take in the holiday splendor from on-high at W Aspen's sky residences.

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Ski season kicks into high gear during the holidays in this Colorado wonderland. December brings fresh powder, the village tree lighting, and New Year's Eve festivities. Vail is known for both good coffee and good cocktails — compare local favorites Yeti's Grind and Loaded Joe's in the morning, and tuck into cocktails at Root & Flower in the evening. You might ring in the New Year at Flame — the fine dining restaurant within Four Seasons Resort and Residences Vail, before innovative cocktails at The Sebastian - Vail, a Timbers Resort. Finally, lay your head to rest at the ever-charming, alpine-chic The Lodge at Vail, a Rock Resort, which boasts a heated outdoor pool flanked with gorgeous fire pits.

Travelers may be drawn to this former artists' colony in Maine as a beach getaway, but the holiday season brings the perks of winter on the sand: lower prices and overall calm, with just enough festivity to keep things humming. Mid-December's Christmas by the Sea festival typically includes a bonfire on the beach and visits with Santa. From Ogunquit, you can also easily reach two shopping areas for getting through your list: the Kittery Outlets and, an hour away, Freeport. For distinctive local shopping, browse the Harbor Candy Shop, where the gift boxes pack in holiday charm.

The banner event during the holidays in this island town started in the 1970s, because too many locals left to shop in Cape Cod. Today, during the annual Christmas Stroll — typically the first weekend in December — you can shop downtown amid dozens of seven-foot, decorated Christmas trees, and take part in wine tastings, ghost walks, and home tours. Pick up some gifts at Murray's Toggery Shop (the mother ship for holiday-ready Nantucket reds) and Jessica Hicks, the boutique of a local jewelry designer. For more tree-gazing, go to the Whaling Museum, which houses 80 trees decorated by local artists, merchants, and kids.

This Florida town lacks snowman-building material, but the snowbird-style winter wonderland still lures holiday revelers with its luxury stores, cool boutiques, and festive ambience. Third Street South is the headquarters for the official tree, evening "snow" showers, and gorgeous window displays, like those at department store Marissa Collections in the Old Naples Historic District. Continue shopping along Fifth Avenue South, and check out whimsical clothing and gift shop Wind in the Willows. 

Breckenridge gets revved up during the holidays, as ski season swings into high gear. Indeed, this resort town skates the fine line between thrills and low stress. During the month of December, festivities abound, from the tree lighting to the Race of the Santas. Travelers will also fall for the charming après-ski options in Breck, from the house-made brews at Breckenridge Brewing to the martinis and flights of Colorado beers at Base 9 Bar.

Grande dame hotel The Greenbrier is the epicenter of the holidays in the Lewisburg area. The 18th-century resort trims the lobby with opulent decorations. Beyond the hotel, the town is peaceful and quietly lit with seasonal lights and low-key attractions.

Winter weather doesn't really kick in until January in this Outer Banks town, so the holiday season is typically still a good time to paddle a kayak or take a boat tour along Taylor's Creek. The Christmas lights take to the water, too: one of the biggest holiday events is the Crystal Coast Christmas Flotilla, a twinkling-lights-strewn boat parade held on the first weekend in December. 

This California town with a rocky coastline doesn't experience much in the way of winter, but the chilly air makes the crashing waves and neighboring wine country seem all the more enticing. Carmel has its own tree lighting — a huge resident tree at the corner of Junipero and Ocean avenues — and the quiet days of early December also make it a little easier to get a table at nearby restaurants like La Bicyclette and Flying Fish Grill. 

The holiday season ushers in serious wattage — star-powered and otherwise — in this Utah mountain town. In late November, Park City lights their iconic tree and celebrates with the annual Electric Parade. During the holidays, kids and sweet enthusiasts of all ages will love the gingerbread display at Montage Deer Valley.

The holiday season coincides with the kickoff of high season in this northwest Florida town. So it's a good place to browse for gifts for everyone on your list. While browsing Santa Rosa, be sure to shop heirloom-quality porcelain at Santa Rosa Pottery and perfect-for-display cookbooks at Kitchen Garden Books & Antiques. 

Late fall and early winter are a good time to score lower rates in this family-friendly town, but that doesn't mean that the place has gone totally quiet. Showstoppers around Myrtle Beach include the twinkling Christmas trees and 2,800 hand-lit candles at Brookgreen Gardens as well as the Festival of Trees— with themed trees for all 50 states — at Ripley's Aquarium. 

History-rich Williamsburg is tricornered hats count as timeless fashion and wreaths hang in every window during December. This time of year also offers plenty of events that let you experience a holiday season like the colonists would: in Jamestown you can watch as wild turkeys are roasted and puddings are prepared, and see how settlers may have observed Christmas.

If a flashing-neon-colored holiday makes you cringe, head to this gorgeous town in Rhode Island, where only white lights are encouraged on homes and restaurants, to conjure an old-fashioned candlelit vibe. Touching on its upscale history, the Mansions of Newport Tour takes you on a stroll through Gilded Age architectural icons like The Breakers, the Elms, and the Marbles, all decked out in sumptuous trees, fine china, and decorations. Since crowds are lighter, it's a good time to try Newport's high-ranking restaurants like the locally sourced Tallulah on Thames.

This military town along the Chesapeake Bay does plenty of pomp, circumstance, and tailgating during the holiday season. Annapolis boasts a plethora of Christmas lights, notably strewn on boats and along the water's edge. Downtown Annapolis also keeps its shops lit and open until midnight on a few Thursdays during December, which is called Midnight Madness.

Forget green: the prime holiday color in this Central Coast town is red, as in pinot noirs, cabernets, and syrahs. During the holidays, wineries offer low-key tastings, music performances, and great gift opportunities; check out Parrish Family Vineyard, whose tasting room is a short walk from downtown's City Park. For some seasonal house envy, go to Hearst Castle, about an hour away, which will be adorned much as it might have been for former resident William Randolph Hearst.

Healdsburg, California is a charming Sonoma County town known for great restaurants and even better — if possible — wineries. Visit Flowers Vineyards & Winery and Aperture Cellars for some warming reds. Don't miss the Flowers' pinot noir, and take in the view at Aperture Cellars, which is magical in any season. If you can make it over to Napa, grab a few bottles to go at Faust (they just debuted a new artist partnership and the bottles now feature sublime artistry, perfect for gifts). Stay the night at Montage Healdsburg, whose charming decor, light-illuminated trees, and roaring fireplaces will put you in the holiday mood. 

Telluride is a pleasantly quirky town and their flair comes through clearly this time of year. The town's big tree lighting happens on the Ski Tree, made of old skis, and accompanies a bonfire comprising more old-and-broken skis. Travelers will love the nightlife in any season. Go barhopping from the cozy lounges of Madeline Hotel & Residences, Auberge Resorts Collection to New Sheridan Hotel's Historic Bar, which has kept the same mahogany-paneled look since 1895.

Bundling up for the holidays in this San Diego enclave means wearing a wetsuit when you surf or stand-up paddleboard — or, on land, perhaps adding a scarf to your ensemble. Indeed, the locals are attractive and stylish, and the area offers both high-end and beachy shopping options. The best dining comes with plenty of cheer at the ever-classy Lodge at Torrey Pines, known for their seasonal, farm-to-table dining.

This waterfront New England town is steeped in history, with settlements dating back to the 1600s. Winter's a festive time to explore its 10-acre time capsule, the Strawberry Banke Museum: during December, you can skate on its open-air Puddle Dock Pond, or walk the candle-box-lined paths to see decorated homes from centuries past. Portsmouth offers one big 21st-century draw, too: tax-free shopping statewide. Load up on classic toys and kids' books in town.

This Jersey Shore town has a strong Victorian streak — its easily recognized by its quaint architecture — and the holiday season pushes it a little further on the Dickensian scale. The walkable Washington Street Mall gets draped in greenery and festive lights. To sweeten the season, drop by the Original Fudge Kitchen, which also offers great fudge-and-saltwater-taffy gift boxes. If you have kids, check in to Congress Hall, where the Grand Lawn across from the beach turns into a seaside winter wonderland complete with festive activities.

During the holiday season, Charlottesville quiets down, as college students cram for finals and then head home. Any visitors get the perk of experiencing the holiday tours of Jefferson's Monticello. Charlottesville scores points for its cool, gift-friendly bookstores like downtown's New Dominion Bookshop.

A casino and boardwalk don't exactly conjure images of plum puddings and carolers, yet travelers appreciate Atlantic City's wild weekend spirit and vivid people-watching around the holidays. Festivities this year include the Tree Lighting and Holiday Musical Light Show at The Quarter at Tropicana. Plus, don't miss the Atlantic City Bazaar at the Noyes Arts Garage of Stockton University.

If holiday stress takes much of the joy out of your world, this quaint wine-country town offers the ultimate antidote: vino and spa remedies. Willow Stream Spa at the Fairmont Sonoma Mission Inn & Spa, for instance, does seasonal treatments worth indulging in. While you're shopping around the town's plaza for relatives back home, you can admire the holiday window displays, then check out the civilized bottles of olive oil and rare artisanal cheeses at gourmet food market Epicurean Connection.

There's no chance of a white Christmas in this mild-weathered Orange County beach town. Instead of watching the sky for snowflakes, you can scan the waves for migrating whales — or focus your attention on the holiday Champagne, spirits, and pastries at the Montage Laguna Beach. The gallery-lined town hosts the Sawdust Winter Fantasy, an arts and crafts festival that spans five weekends in November and December, to get visitors into the holiday spirit.