15 Memorable Holiday Road Trips to Virginia’s Most Festive Towns

The holidays are some of the most beautiful times of the year in Virginia, with lights, garland, and stunning seasonal décor going up all around the Commonwealth. But while every town and city puts on a show, some go above and beyond with their decorations, and these destinations are a must if you’re looking to hit the open road and enjoy a spirited road trip during the holiday season.

From the charming small towns where you can peruse locally-owned boutique shops to the urban centers illuminated by countless holiday lights and packed with shopping opportunities, plan a road trip to a few of these 15 decked-out destinations to fill your holidays with unforgettable cheer this year! 

FESTIVE TOWNS IN THE SHENANDOAH VALLEY & VIRGINIA MOUNTAINS

STAUNTON

Photo Credit: Warren Faught

During the holidays, downtown Staunton decorates the shop windows with festive touches, and holiday lights are wound along the city’s roadside light posts, creating a picturesque scene that brings to mind Norman Rockwell artwork. The city hosts two must-see light events; the two-mile drive-by or walk-by Celebration of Lights at Gypsy Hill Park, a free event, and the Avenue of Evergreens, a light display at the historic Blackburn Inn for guests staying overnight. 

Where To Grab Delicious Holiday Treats: Reunion Bakery | Yelping Dog Wine | Ox-Eye Vineyards Tasting Room | The Split Banana | Firkin Pie Company | Cocoa Mill Chocolatier

Where to Snap Holiday Photos: The Marquis Building | Sears Hill Pedestrian Bridge

Where to Shop Local: 

• Blair Made: Custom-crafted farmhouse-style wooden signs.
• Jude’s, A Fine Emporium: Gorgeous collection of gifts and wearables.
• Made: For the People, By The People: Domestically made, with sass.
• Art for Gifts at the Staunton Augusta Art Center: A unique boutique holiday shopping experience featuring handmade fine arts and crafts by over sixty local and regional artists.
• Heirloom Home: Tabletop decor and linens, including luxury Sferra bedding.
• Latitude’s Fair Trade: Artisanal gifts from around the world.
• Pufferbellies Toys and Books: Best. Toystore. Ever.
• ALI & Co.: Custom-crafted apothecary items.
• Beverley Street Cigar Co.: Cigars, pipes, and fine tobacco.

LEXINGTON

Downtown Lexington offers the perfect spot for a festive holiday outing. The lamp posts don wreaths with big red bows while local shopkeepers create beautiful displays in their front windows. And that’s just the outside! Fuel up at local eateries with holiday fare before hitting the shops, then reward yourself with a craft beer or creative cocktail after you’ve crossed everyone off your list. Plan an overnight stay at The Georges for their Cookie Decorating & Holiday Movies event for a holiday-inspired weekend getaway. 

Where To Grab Holiday Goodies: Sweet Treats Bakery | Sweet Things Ice Cream Shoppe  | Cocoa Mill Chocolate Co. 

Where to Snap Holiday Photos: Natural Bridge State Park LoveWork | Luminary Nights | Lexington Christmas Tree in Hopkins Green 

Where to Shop Local: 

Sugar Maple Trading Company: Locally-owned gift shop where you can find those perfect gifts for everyone in your family.

Walkabout Outfitter: Outdoor gear shop that carries hiking, backpacking, camping equipment, and more much.

ROANOKE

Photo Credit: Shannon Terry

Many local shops in Downtown Roanoke display their holiday spirit with festively extravagant storefront window displays, especially on Market Street. For the first three weekends in December, Dickens of a Christmas brings charming holiday traditions to the heart of Downtown Roanoke; chestnuts roasting on an open fire, Dickens-esque carolers, and local artisan vendors at the Historic Roanoke City Market are a few highlights of this seasonal celebration. 

Where To Grab Holiday Goodies: 1882 Lobby Bar & Pine Room Restaurant at the Hotel Roanoke | Evie’s Bistro & Bakery

Where to Snap Holiday Photos: Christmas Tree at the City Market Building | Downtown Roanoke’s LoveWork | Explore Park’s Illuminights

Where to Shop Local: 

• The Historic Roanoke City Farmers’ Market: Open 363 days a year and features local, handmade goods from artisans around Virginia’s Blue Ridge. 
• Black Dog Salvage: Premiere salvage warehouse filled with salvaged architectural antiques and home of the DIY Network’s television series, Salvage Dawgs.
• Chocolatepaper: Gourmet chocolate shop and a quirky selection of gifts and cards. 

NARROWS

Photo Credit: Tim Williams

A small rural community on the banks of the New River in Southwest Virginia, Narrows has all sorts of holiday fun, from a holiday parade to a Farmers Market with seasonal activities, murals, and locally made goods. The holiday decorations in Narrows span the Route 460 bridge and line the streets with lights and vignettes. The Narrows Duck Pond, in downtown and across the street from the Farmers Market, is uniquely decorated for the holidays, with lights strewn amongst the trees and islands of Wolf Creek.

Where To Grab Holiday Goodies: Anna’s Restaurant

Where to Snap Holiday Photos:  LoveWork & Light Displays at the Duck Pond | Main & Monroe Streets Mural & Holiday Decor 

Where to Shop Local:  

• Narrows Farmers Market: Shop locally-made goods at the variety of booths. Seasonal events posted on social media and held throughout the holiday season. 
• Pearis Mercantile: In the neighboring town of Pearisburg, Pearis Mercantile has fun gifts for all occasions, including seasonal items, home decor, jewelry, and much more!

FESTIVE TOWNS IN NORTHERN VIRGINIA

LEESBURG

The postcard-worthy streets of Downtown Leesburg in Northern Virginia come alive during the holidays. A Christmas tree shines bright in the Town Square, while the chic boutiques, restaurants, and bars on King and East Market streets glow with the sparkle of decorative lights and the historic street lamps shine bright with red ribbons and greenery. Be sure to get tickets to the Old Lucketts Store Holiday Open House, where the famed antique store transforms into a Winter Wonderland. All decorations are available for purchase and the shop is a great place to get holiday photos with your loved ones! 

Where To Grab Delicious Holiday Treats: Echelon | SideBar | Tuscarora Mill | Mom’s Apple Pie | Mocatinas

Where to Snap Holiday Photos: W&OD Trail LoveWork | Discover the Charm Mural | Leesburg Courthouse | The Old Lucketts Store

Where to Shop Local: 

• Muz and Rose: New to the Leesburg shopping scene, this boutique features items from local artisans. 
• Brick & Mortar: This trendy shop features a variety of home décor items as well as unique finds like whiskey-flavored toothpicks. 
• The Very Virginia Shop: From Virginia peanuts to Virginia is for Lovers swag, this shop is a must to pick up a Virginia souvenir. 
• The Old Lucketts Store: Antique shop carrying goods from over 20 different dealers. 

MIDDLEBURG

Photo Credit: Fred deSousa

Middleburg is well known for their famous annual holiday parade, led by dashing horses and hounds that are part of the region’s “Hunt Country” vibe, but this year, the town is celebrating in a new way to accommodate safety guidelines. Visitors can partake in a family-focused scavenger hunt around town, enjoy free hot cocoa at various stops, drop letters to Santa at the local post office, and take a carriage ride to see the sights.

When it comes to holiday decor, Middleburg’s picturesque historic downtown looks like a scene straight from “A Christmas Carol”. Washington Street is decked out with twinkling lights, antique wooden Christmas ornaments adorn the light posts, shop windows are dressed to the nines as part of a holiday window decorating contest, and the town’s gorgeous Christmas tree glistens outside the local Visitor Center. Couple the holiday décor with the crisp December air and it’s magical.

Where To Grab Holiday Goodies: King Street Oyster | Red Fox Inn & Tavern | Knead Wine | Salamander Resort & Spa | Little Apple Pastry Shop

Where to Snap Holiday Photos: Red Fox Inn & Tavern | Salamander Resort & Spa

Where to Shop Local: 

• The Fun Shop: Family-owned specialty department store that has been a town staple since 1956 and features children’s toys and books, home and holiday décor, hunt country gifts, and more.
• The Christmas Sleigh: Authentic German Christmas gifts in the heart of Middleburg. 
• Chloe’s of Middleburg: Apparel, accessories, and hand-poured Middleburg candles to bring the ambiance of town right to your home.

ALEXANDRIA

Photo Credit: Kristian Summerer for Visit Alexandria

Strolling down King Street in Old Town Alexandria feels as if you’re in a real-life Dickens Village, complete with European flair. The cobblestone streets are alight with lights strung from almost every shop. Stop into a few of the boutique shops that line King Street for some holiday shopping and be sure to check the Alexandria events page before you visit to see if the Del Ray and Carlyle neighborhoods are hosting any holiday markets, where you can sample local baked goods and peruse handmade gifts. While in Alexandria, don’t miss Ice & Lights: The Winter Village at Cameron Run, which will have an ice rink, over a dozen holiday light displays, food, seasonal music, and much more. 

Where To Grab Holiday Goodies: Alexandria Pastry Shop | Alexandria Cupcakes | Lavender Moon Cupcakery | La Madeleine French Bakery & Cafe

Where to Snap Holiday Photos: Old Town Alexandria Harbor | Alexandria’s Waterfront Park | Along the cobblestone streets of Old Town Alexandria | Founders Park | Ice & Lights: The Winter Village at Cameron Run

Where to Shop Local: 

• Threadleaf: Independent boutique with fashion-forward clothing and accessories that are responsibly made and environmentally-friendly. 
• Old Town Books: Independent book store in Old Town Alexandria. 
• The Hive: Women’s designer clothes, shoes, accessories, & jewelry. 
• She’s Unique Jewelry & Gifts: Carefully curated selection of modern and elegant jewelry. 
• The Hour Shop: Vintage designer cocktail sets and barware. 
• Red Barn Mercantile: Family-run boutique specializing in home furnishings, accessories, linens, and other home decor and unique gifts. 

FREDERICKSBURG

The holidays are absolutely magic in historic Downtown Fredericksburg, especially along Caroline Street. The street runs through the center of a 40-block National Historic District that is lined with original 18th and 19th century buildings all decked out for the holidays with festive lights, and decorations adorn the street’s light poles and storefront windows. Each shop along Caroline Street puts their all into their holiday decorations, creating bright and beautiful displays that are sure to wow visitors. If you’re staying into the evening, book an Olde Towne Jingle Bell Carriage Ride to see the holiday decorations and enjoy a romantic ride through downtown Fredericksburg.

Where To Grab Holiday Goodies: Eileen’s Bakery | Fredericksburg Cupcake | FoodE | A. Smith Bowman Distillery

Where to Snap Holiday Photos: The Kenmore Inn | Chatham Manor | LoveWork in Hurkamp Park | Market Square Alley’s Laser Lights Display

Where to Shop Local: 

• Monkee’s of Fredericksburg: Trendy women’s clothing & accessories boutique.
• Made in Virginia Store: Shop that carries all sorts of Virginia-made goods and products, from gift baskets filled with Virginia foods to clothing and home decor. 
• Jabberwocky Children’s Books & Toys: Children’s bookstore that also has an array of unique games and toys.
• Latitudes Fair Trade Store: Virginia-based shop that sources handmade goods from all over the world while supporting third-world countries through fair trade practices. 
• Sugar + Spruce: Skincare and soap shop that crafts clever products in the shape of your favorite candies and sweets such as bath bombs in the shape of colorful donuts. 

FESTIVE TOWNS IN COASTAL VIRGINIA

VIRGINIA BEACH

Want to see the lights safely from your car? Head to Virginia Beach and follow along Atlantic Avenue to see the Boardwalk’s festive nautical-themed holiday lights display. You can even pair the lights with a customized holiday soundtrack that plays on the radio. Seasonal decorations include illuminated fish, musical crabs, and elves joining the surfing Santa, as well as a new 40-foot tall dancing Christmas tree. Advanced tickets required. After enjoying the lights display, head to The Alley in the ViBe District for a little holiday shopping and some festive treats. 

Where To Grab Holiday Goodies: Three Ships Coffee | The Pink Dingy | May’s Parlor | The Hunt Room at the Cavalier Hotel

Where to Snap Holiday Photos: ViBe Creative District Murals | Holiday Light Displays off the Boardwalk 

Where to Shop Local: 

• Virginia Beach Christmas Market: Over 250 artisans showcasing their locally-made goods. Happening November 26-28, 2021 at the Virginia Beach Convention Center. 
• North End Bag Co.: Handcrafted canvas and leather goods company specializing in totes, purses, duffel bags, wallets, and more. 
• Jar of Dust: High-quality functional stoneware ceramics including mugs, wall tiles and soap dishes as well as hand blown glasses and vases; in the ViBe District. 
• Igor’s Custom Signs & Pinstriping:  Virginia Beach artist Igor handpaints special Christmas ornaments for sale at his studio. 
• Glow Apothecary: Pampering wellness gifts, cleansing skincare, and beauty products plus gift sets and a kid-friendly Littles section.  
• Mrs. Bone’s: Custom handmade dog collars and leashes that will make sure your pet enjoys the holidays in true festive style. 

KILMARNOCK

Located in Virginia’s River Realm, Kilmarnock was chosen as Eastern Virginia’s Favorite Main Street by Virginia Living Magazine. During the holidays, Kilmarnock is filled with holiday cheer as the Main Street business fronts get creative in the shop windows and festive accents are seen throughout the town. A LoveWork is decked out in holiday garb, and Kilmarnock’s Christmas in the Park event at Town Centre Park features the tallest Christmas tree in Lancaster Town as well as thousands of holiday lights strung through the park. 

Where To Grab Holiday Goodies: Northern Neck Popcorn | Lee’s Restaurant 

Where to Snap Holiday Photos: LOVE Sign Christmas | Holiday Selfie Station at Town Hall

Where to Shop Local:  

• Steptoe’s District: An open-air shopping mall featuring 50+ businesses. 
• The Rivah: Women’s clothing store and gift shop carrying brands like Simply Southern, Kendra Scott, and Lilly Pulitzer. 
• Pearl Boutique: Artsy, comfortable women’s apparel, jewelry, and artisan gifts. 
• Weekends Fashions for Him and Her: Luxury women’s and men’s clothing shop. 
• Waterline: Coastal clothing shop for women. 
• Grow: Retail shop carrying fun gifts like DIY terrariums and artwork. 
• Burkes Jewellers: Hometown jewelry store on Kilmarnock’s Main Street.  
• Ross Jewelers: Locally owned fine jewelry shop. 

CAPE CHARLES

Photo Credit: Rachel Stevens

On the southwestern side of Virginia’s Eastern Shore, Cape Charles is a small bayside town that celebrates the holidays with coastal flair. Every Friday beginning the last weekend of November, the town hosts Festive Fridays, with discounts at restaurants and stores, family-friendly entertainment like a holiday choir, a live magician show, and balloon artists. 

Carriage rides are offered through downtown Cape Charles, and outdoor holiday movies are projected in the evenings on the side of Bailey’ Bait & Tackle on Mason Avenue. Kids can see Santa and Mrs. Claus in their workshop and write letters from a magical mailbox that goes straight to the North Pole. 

Where To Grab Holiday Goodies: Coastal Baking Company | Cape Charles Candy Company | The Bakery on Mason | Cape Charles Coffee House

Where to Snap Holiday Photos:  Cape Charles LoveWork | Cape Charles Fishing Pier

Where to Shop Local: 

• Voiajer: Eco-friendly gift shop carrying fair trade goods made all around the world. 
• Moonrise Jewelry: Unique handmade jewelry incorporating stunning materials like exotic orchid blossoms or colorful fish leather. 
• Chuckletown Productions: Creative shop with a wide array of apparel, jewelry, glassware, souvenirs, and kids toys and games. 

WILLIAMSBURG

Williamsburg will have holiday lights and decorations spread all over the city, but a great place to get a walking tour filled with seasonal touches is to head to Colonial Williamsburg’s Dukes of Gloucester Street (also referred to as DoG Street). This historic attraction serves festive treats at their colonial-era restaurants, including warm spiced cider, and during the holidays, the stately colonial homes are decked out in traditional holiday touches, such as fresh greenery and fruit.

In addition to stunning classic decorations, Colonial Williamsburg hosts several historic seasonal events, such as a Grand Illumination Holiday Feast at Chownings’ Tavern, a Holiday Decoration Workshop, and guided Christmastide Tours. Their biggest event, the Grand Illumination, occurs on December 2-4, 9-11, & 16-18 this year (2022) and features the new Procession of the Yule Log and holiday songs and stories on Market Square as well as the Grand Illumination firework displays on Saturdays.

Where To Grab Holiday Goodies: Chowning’s Cider Stand | Raleigh Tavern Bakery | Williamsburg Inn | Blackbird Bakery

Where to Snap Holiday Photos: The Williamsburg Inn | Along Dukes of Gloucester Street | The Capitol Building | The Governor’s Palace

Where to Shop Local: 

• Wythe Candy & Gourmet Shop: The region’s largest selection of candy, offering gourmet items like fresh-dipped caramel apples, artisan chocolates, and handmade fudge. 
• Williamsburg at Home: Furniture and home decor store in Colonial Williamsburg.
• Prentis Store: 18th-Century gifts and goods by tradesmen, like handcrafted leather goods, iron hardware, tools, reproduction furniture, pottery, and writing instruments. 
• Brick & Vine: Homemade furnishings, craft beer, wine, gourmet food and seasonal decorations all in one stop.
• The Peanut Shop of Williamsburg: Virginia peanuts and peanut products in dozens of flavors. 

FESTIVE TOWNS IN CENTRAL VIRGINIA

RICHMOND

The capital city goes all out for the holidays, with most neighborhoods putting up their own display of lights and decor, but if you’re looking for a one-stop shop for all of your holiday gift needs in the Richmond region, visit Carytown. Most shops offer holiday-themed gifts, items, and sales, and the street is lined with decorations, including window displays and lights strewn through the trees along the road. Order a few to-go holiday cocktails from The Jasper’s seasonal pop-up bar, Miracle on Cary Street, for outstandingly merry drinks that are sure to add to your holiday cheer. 

After shopping, strolling, and dining in Carytown, head to Downtown Richmond and catch the city skyline illuminated by holiday lights, or drive out to Lewis Ginter Botanical Garden for the Dominion GardenFest of Lights, where the trees, bushes, and other plants are strung with thousands of glittering lights that illuminate the entire garden. 

Want to catch even more holiday lights without worrying about COVID-19? Get tickets to the Illuminate Light Show at Meadow Event Park in Doswell, Central Virginia’s largest drive-through light show that is synchronized to holiday music. 

Where To Grab Holiday Goodies: The Jasper | Shyndigz | Can Can Brasserie | Carytown Cupcakes | Belmont Butchery

Where to Snap Holiday Photos: Byrd Theatre | Lewis Ginter’s Dominion GardenFest of Lights | Downtown Richmond’s 

Where to Shop Local:

• Mongrel: Boutique shop that carries everything from birthday cards and books to home decor and unique trinkets. 
• Plan 9 Records: Locally-owned music shop carrying vinyl records, CD’s, and music-related gear. 
• World of Mirth: Eclectic toy shop.  
• Bygones Vintage: Vintage clothing shop carrying women’s and men’s clothing that spans decades. 
• Beasties: Unique, quirky, and snarky finds. Carries an assortment of gifts for any occasion.
• Ashby: Trendy women’s and men’s consignment clothing store.
• Ladles & Linens: Home goods and kitchen shop in Carytown. 

ASHLAND

Photo Credit: Michael Simon, @michaelsimonphoto

Located about 15 miles north of Richmond right off Interstate 95, Ashland is a small town with a big personality. Train tracks run the length of Ashland’s main street, which is lined with boutiques, restaurants, a historic inn, a brewery, and more. 

Each December, Ashland puts on the Light Up The Tracks event, where the main street and train tracks transform into a vintage holiday village. Visit this pristine small town during this holiday event and take in the magic of the nostalgic decor. 

Where To Grab Holiday Goodies: Homemades by Suzanne | Sugar Fix Bakery | The Caboose

Where to Snap Holiday Photos: Light up the Tracks event | Henry Clay Inn | Ed Trask Mural | The Ashland Theatre

Where to Shop Local:  

• Tiny Tim’s Train & Toys: Toy store that carries a huge selection of model trains.
• Ashland Meat Company: Butcher shop offering all sorts of meat cuts, both prepackaged and cut fresh for customized orders, as well as an array of gourmet food products. 
• Origin Beer Lab: Local craft brewery; grab a six pack for all your beer-loving friends and family members! 

CHARLOTTESVILLE

Photo Credit: Brantley Ussery

The shops along Charlottesville’s Downtown Mall get into the holiday spirit with lots of lights, garland, and seasonal decor. Take it all in as you walk along this outdoor pedestrian mall, which is lined with excellent boutique shops perfect for finding that holiday present as well as locally-beloved restaurants serving all sorts of festive treats. Shop, eat, and enjoy the merriment with a visit to the Downtown Mall! 

Where To Grab Holiday Goodies: The Alley Light | Kilwin’s Charlottesville | Mudhouse Coffee | The Pie Chest | Petite MarieBette

Where to Snap Holiday Photos: On The Lawn at University of Virginia | At Nearby Monticello | In front of decorations on the Downtown Mall | Boar’s Head Resort

Where to Shop Local: 

• Pawprints Boutique: Gifts and apparel for dog and cat lovers; treats, collars, and other goodies for their pets. 
• BitterSweet: Trendy women’s fashions and accessories. 
• Low: Vintage records, clothing, & antiques. 
• Alakazam Toys & Gifts: Wacky toy store with gifts for all ages. 
• C’Ville Arts Cooperative Gallery: Storefront featuring handmade works by many Virginia artists and craftspeople.

Looking for more holiday cheer in Virginia? Here are a few more towns and cities that go big for the season!

• Chincoteague
• Norfolk
• Front Royal
• Floyd
• Reston  
• Woodstock
• Winchester
• Fincastle
• Salem
• Onancock 
• Bristol 
• Abingdon