Nantucket, Massachussets. Photography by Rebecca Love Photography.
With their festive Main Streets, friendly locals, and time-honored traditions, small towns can be the perfect destinations during the holiday season when you’re seeking a little good cheer. To prove this point—and provide some inspiration for planning a getaway—we asked three of our editors who live in places that truly turn on the charm during December to share their must-sees-and-dos for a holiday season visit to their areas. From a German celebration in Texas Hill Country to a summer vacation spot-turned-winter wonderland to a magical experience in Hunt Country, Virginia, prepare to want to pack your bags.
While widely known as an ideal summer destination, Nantucket is equally delightful during the holiday season. In fact, The Scout Guide Nantucket editor Stacey Leuliette says that one her favorite times of year on the island is the first weekend in December after Thanksgiving, thanks to the annual festivities that take place. “The Christmas Stroll is a big deal here in Nantucket, going into its 47th year,” she explains. “The whole town is abuzz with holiday cheer!” Originally created by the town’s Chamber of Commerce to encourage islanders to shop local during the holidays, it has since grown from a three-hour event to a three-day holiday extravaganza that is a draw for locals and visitors alike.
Photography by Rebecca Love Photography.
Nantucket Christmas Stroll. Now in its 47th year, the island’s world-renowned signature event referred to by locals simply as “Stroll” takes place the first weekend of December (this year it will be December 3 to December 5), featuring the eagerly anticipated arrival of Santa via his nautical “sleigh” at noon on Saturday. A host of holiday activities, including strolling carolers in Victorian garb, the Magical Talking Tree, craft shows, a European-style Christmas Marketplace, and more ensure fun for the entire family.
Annual Christmas Tree Lighting Ceremony and Community Caroling. Nantucket Noel kicks off at dusk on November 26 with the annual Tree Lighting and Community Caroling Ceremony presented by Stop & Shop. While it’s a wonderful in-person event, this year, no matter where you are, you can enjoy the ceremony, as the illumination of more than 150 balsam trees on Main Street will be livestreamed on the Nantucket Chamber of Commerce’s Facebook and Instagram.
Red Ticket Drawing. To encourage shopping local for the holiday season and promote the sustainability of island commerce, the Nantucket Chamber of Commerce continues its popular Holiday Red Ticket Program, with participating Chamber member businesses giving out one red ticket for every $25 spent. At 3:00 p.m. on December 24, five lucky winners of $1,000, and one extra-lucky winner of $5,000, will be chosen at random from the multitude of tickets filling the enormous bed of a Don Allen Ford truck.
STAY THE NIGHT
If you want to rest your head at a luxurious resort right on the harbor, book a room at White Elephant. When you’re visiting with family in tow, Stacey recommends Harborview Cottages, which allows guests to have their own place to relax while enjoying all the amenities of a hotel. For design-focused travelers, Stacey suggests Hotel Pippa, which has the perfect quintessential Nantucket vibe with incredible style, in addition to a busy restaurant. Finally, Jared Coffin House, recently reopened in April 2021, is a landmark inn situated in the heart of the island’s historic district.
STOPS FOR SANTA’S HELPER
For a curated selection of vintage finds—plus wine and cheese, visit Current Vintage. For contemporary pieces for the ladies on your list, stop by Grace Geier and Dawn. As a designer herself, Stacey is always looking for beautiful home furnishings, and 28 Centre Point is among her favorite stops for Nantucket-chic home accessories. A visit to Nantucket wouldn’t be complete without a trip to the retail legend Murray’s Toggery Shop, known as the town’s department store with everything you need to dress on the island. Visitors will also be delighted when they pop into Bookworks, a lovely little book and gift shop.
EAT, DRINK, AND BE MERRY
Primarily closed during the off season, Or The Whale is open during Christmas Stroll for delectable dinners, and reservations are advised. Stacey loves to visit Via Mare for the Venetian-inspired small lights highlighting the garden and the sea. Right outside of town you will find Cisco Brewers, a Nantucket institution where locals gather to listen to live music and sample food truck fare and beer flights.
HUNT COUNTRY, VIRGINIA
Photography by Middleburg Photo.
The holidays in Hunt Country bring to mind scenes from Downton Abbey, with over 100 horses and riders attired in scarlet fox hunting jackets parading down the brick-lined street, followed by a regal pack of hounds. Nelina Loiselle, editor of The Scout Guide Hunt Country, explains that while the Christmas in Middleburg parade is a highlight, the best local boutique shopping, historic towns decked to the nines, tree lightings, and wine tastings keep Hunt Country bustling with magic for the holidays.
Christmas in Middleburg Event and Parade. On December 4, you don’t want to miss out on this beloved Hunt Country tradition where locals and visitors from all over line up for the Hunt & Hound reveal at 11:00 a.m. down Middleburg’s quaint village streets. If you have kids in tow, Nelina advises arriving at 8:00 a.m. for breakfast with Santa, then hit the craft fair and visit one of their local boutiques before the parade begins.
Middleburg Tree Lighting and Carols Ceremony. On Friday, December 4 at 5 p.m., the revelry continues in Middleburg with the annual lighting of the tree, which takes place behind the Pink Box.
A Rappahannock Winter Wonderland. During the entire month of December, participating shops, restaurants, wineries, breweries, and galleries in this region will be decorated and offering handmade goodies and special sales. A kick-off event is planned for December 5, and Nelina recommends a walk through the fairy tale-like town of Little Washington, a drive down scenic Fodderstack Road, lunch at The Blue Door Kitchen & Inn, and shopping in the nearby village of Sperryville.
STAY THE NIGHT
The Salamander Resort is the area’s only five-star luxury property right in the heart of Middleburg, and according to Nelina, it’s the perfect home base for the Christmas in Middleburg parade weekend. Be sure to schedule some spa time (pro tip: Nelina says to book in advance and ask for Brian!) and grab a drink from the Gold Cup wine bar’s billiard room for a round of pool by the fire. Alternatively, plan a stay at Glen Gordon Manor boutique inn for a magical holiday getaway. Spend the day exploring the Rappahannock Winter Wonderland festivities, then head back to your cozy room or warm up with a drink in the Hunt Room before feasting on Chef-Owner Dayn Smith’s five-course meal for supper. For a true horse country estate just a quick scenic jaunt from Middleburg, plan to stay at The Welbourne Inn. This (very reasonably priced) bed-and-breakfast dates from 1775 and is brimming with centuries of American history.
Photography courtesy of Crème de la Crème.
STOPS FOR SANTA’S HELPER
Stop by Creme de le Creme for French and Italian gifts, tableware, inspired objects, ornaments, and one-of-a-kind finds. Nature Composed showcases handmade wreaths, in addition to holiday plants and garden gifts. For stylish clothes and accessories, visit Chloe’s of Middleburg and Zest Clothing & Co. At Tri-County Feeds, Fashions, Finds, Hunt Country’s favorite country lifestyle store, you’ll be able to score gifts for just about everyone on your list. Finally, Atelier Design & Decor is the spot to discover sophisticated gifts, home and holiday decor, art, and furniture curated by designer Terri Pakravan.
EAT, DRINK, AND BE MERRY
Nelina warns that the restaurants in Middleburg get packed on parade day, so a 10-minute drive to the Market at Bluewater Kitchen might be a good option for a sit-down meal, or you can peruse their grab-and-go case for seasonal fare made with fresh local ingredients. After a day of shopping in Middleburg, snag a seat at a fireside pit at Greenhill Winery and unwind with a glass of Blanc de Blanc while taking in the sweeping views of the Blue Ridge Mountains. For post-parade drinks or a fireside supper, Nelina likes to visit Red Fox Inn, where their fried chicken dinner is legendary. Before leaving town, stop at The Whole Ox for gourmet items, fine wines, and full-service butchery serving the best burgers, sandwiches, and fries (Nelina recommends that you get all the sauces!).
Photography by Downtown Decorations Incorporated.
Nestled in the heart of the Texas Hill Country, Fredericksburg delivers a Norman Rockwell-esque holiday experience. The Scout Guide Hill Country editor Francie Mannix explains that the area was founded in 1846 by German settlers who left their mark on this quaint, unique town, as seen in their architecture, food, festivals, and their affinity for celebrating the Christmas holiday, known as Weihnachtszeit. “During the holidays, everything is centered around the Marketplatz, the town square, where a giant 30-foot Christmas tree and 26-foot traditional German Christmas pyramid, complete with moving wooden figurines, dominate the square,” Francie says. “You can take a turn ice skating at the Eisbahn rink, pop in and out of the bedecked shops lining Main Street, or enjoy the wine trail and local cuisine. However you choose to spend your time, Fredericksburg is the perfect holiday getaway.”
Santa Parade and Lighting of Christmas Tree. Happening the first Friday after Thanksgiving, this highly anticipated annual event draws locals and visitors alike.
Fredericksburg’s Christmas Nights of Lights. Running nightly from November 23, 2021 to January 6, 2022, all are invited to enjoy a festive evening starting at 5:00 p.m. that includes holiday carols, music, and an oral history of Christmas in Fredericksburg, concluding with the lighting countdown of the Marktplatz.
64th Christmas Home Tour and Market. On December 4 from 11:00 a.m. to 4:00 p.m., the annual self-guided Christmas Home and Tour will commence, featuring beautiful homes in and around Fredericksburg all decked for the holidays. Additionally, 21 boutique vendors will sell unique gifts, food, and holiday items at the market. Tickets for the event can be purchased here.
STAY THE NIGHT
While visiting Fredericksburg, you can stay at the numerous bed and breakfasts from converted Sunday houses to one-bedroom homes that you can book through Absolute Charm or Gastehaus Schmidt. Hoffman Haus, The Evers House or The Winchester Lodge are also great options. The newest spot on the scene, True Heart Hotel, is garnering lots of buzz.
Photography courtesy of Carol Hicks Bolton Antiques.
STOPS FOR SANTA’S HELPERS
There are lots of shops along Main Street, including Vaudeville, a must-visit featuring an art gallery and wonderful gifts. Francie recommends you also wander down some of the side streets to Carol Hicks Bolton Antiques, Blackchalk Home and Laundry, and Simple Home Goods for great finds.
EAT, DRINK, AND BE MERRY
Francie’s favorite spot for breakfast is Emma and Ollie, and for lunch she recommends Woerner Cafe and Tubby’s. For a traditional German dinner, stop at Otto’s . Sage, Martini’s Seafood House, Hill and Vine, and Chase’s Place are all also well worth a visit for dinner. If you’re looking for fine dining, Francie recommends Vaudeville Bistro.
Find a full list of our scouted cities here, and use The Scout Guide as a resource for local recommendations the next time you travel.