9 Romantic Small Towns In Virginia For A 3-Day Weekend
Virginia presents a landscape that feels designed for reconnection. From the jagged peaks of the Blue Ridge to the tidal marshes of the Eastern Shore, the state provides a variety of settings for a three-day escape. For couples or retirees, the appeal often lies in the slower rhythms found away from the congestion of Northern Virginia or Richmond. These nine destinations, all maintaining populations well under 50,000, emphasize local heritage and scenery over modern noise. You might find yourselves watching wild ponies at sunrise or watching a Shakespearean play in a faithful replica of a 17th-century theater. Each entry prioritizes specific local landmarks and dining spots to ensure your itinerary stays grounded in the actual character of the community rather than vague travel tropes.
Onancock
Onancock's deep-water harbor and streets lined with Victorian homes serve as the perfect backdrop for a thriving art scene. The community attracts painters, sculptors, and glassblowers from across the region, a creative energy that contributed to the town being named one of the "Coolest Small Towns in The South" by Budget Travel magazine. While Captain John Smith first mapped the area in the 1600s, the well-known nickname "Gem of the Eastern Shore" is a cherished modern tribute. Stay at The Charlotte Hotel and Terra Mare Restaurant, a boutique property on North Street with an attached full-service bar, or book a room at The Inn at Onancock, where innkeepers host an evening "wine down" on the porch. Take the seasonal ferry from Onancock Wharf to Tangier Island, an isolated crabbing community known for its distinct local culture. Back on the mainland, catch a first-run film at the Roseland Theatre, a 1950s movie house that also hosts an International Film Festival. Dine on dock-to-dish seafood at Bizzotto's Gallery Caffe or enjoy waterfront views at Mallards at the Wharf, housed inside the historic Hopkins & Bros. Store. The North Street Playhouse stages year-round live theater productions, and monthly Second Fridays keep galleries open late for evening browsing.
Middleburg
Known as the "Nation's Horse and Hunt Capital," Middleburg sits in the heart of Virginia's wine country, just an hour from Washington, D.C., yet worlds away in atmosphere. Retired couples come here for vineyard-hopping and equestrian elegance at a gentler pace. Salamander Middleburg, a 340-acre resort in the foothills of the Blue Ridge Mountains, pampers guests with a full-service spa, horseback riding, and farm-to-table dining at Harrimans Grill. For a more intimate stay, The Red Fox Inn & Tavern, operating since 1728, delivers candlelit romance in stone-walled dining rooms. Spend an afternoon at Boxwood Estate Winery or Chrysalis Vineyards, then browse the boutiques along Washington Street. The National Sporting Library & Museum displays centuries of equestrian art and memorabilia, including a handwritten essay by Teddy Roosevelt defending fox hunting.
Lexington
Southern Living named Lexington Virginia's "Most Romantic Winter Getaway," and it earns that title year-round. This Shenandoah Valley college town, home to Washington & Lee University and Virginia Military Institute, wraps 19th-century brick architecture around a lively food and arts scene. The Georges, a boutique inn spread across five historic buildings on Main Street, puts guests steps from everything. Dine at Haywood's Restaurant for live jazz on Sunday evenings, or grab handmade gelato at Sweet Things Ice Cream Shoppe. Book a horse-drawn carriage tour with Lexington Carriage Company to clip-clop past historic mansions and sidewalks laid with distinctive Lexington brick. Day-trip to Natural Bridge State Park, where Thomas Jefferson once owned the 215-foot limestone arch, or catch a summer show under the stars at Lime Kiln Theater. Hull's Drive-In, one of the last drive-ins in Virginia, screens double features on weekend nights.
Staunton
Pronounced "STAN-ton," this architectural gem in the Shenandoah Valley showcases over 200 buildings designed by architect T.J. Collins between 1890 and 1911, no two alike. The American Shakespeare Center's Blackfriars Playhouse is the world's only recreation of Shakespeare's original indoor theater, making date night feel like time travel. Stay at Hotel 24 South or The Blackburn Inn and Conference Center, both set in beautifully restored historic buildings with on-site dining. Mornings call for French pastries at Réunion Bakery & Espresso, followed by wine tasting at Ox-Eye Vineyards. The farm-to-table dinner at Zynodoa Restaurant highlights Southern cuisine made from local ingredients like Polyface Farm chicken. Visit the Woodrow Wilson Presidential Library&Museum to see where the 28th president was born, or watch live glassblowing demonstrations at Sunspots Studios.
Abingdon
Deep in the southwest corner of the state, Abingdon is defined by its roots in the arts. Barter Theatre, founded in 1933 when patrons traded produce for admission during the Depression, launched the careers of Gregory Peck and Ernest Borgnine. It remains America's longest-running professional theater, staging 17-19 productions annually. Check into The Martha Washington Inn & Spa, a four-star historic property built in 1832 that has served as a private residence, a Civil War hospital, and a women's college before becoming a hotel. Retired couples will appreciate the Virginia Creeper National Recreation Trail, a 34-mile rail-trail perfect for leisurely biking. The Tavern has operated since 1779 and is recognized as the oldest bar in Virginia. Find the perfect cup of ethically sourced coffee at The Girl & Raven on Main Street, then browse local crafts at Holston Mountain Artisans Cooperative.
Floyd
This one-stoplight town on the Blue Ridge Plateau has drawn artists, musicians, and creative spirits since the 1970s. Floyd sits just six miles from the Blue Ridge Parkway and anchors Virginia's Heritage Music Trail, known as The Crooked Road. The legendary Floyd Country Store, a 115-year-old general store with barrels of old-fashioned candy near the entrance, hosts the Friday Night Jamboree, a nearly 40-year tradition of bluegrass, old-time, and gospel music that fills the dance floor with flatfoot dancers. Free Sunday afternoon jams welcome all skill levels. Stay at Hotel Floyd, an eco-friendly lodge built with sustainable materials and furnished with locally crafted pieces. Drive the Parkway to Mabry Mill, the most photographed spot in Virginia, where a historic water-powered gristmill still operates. Couples can sample wines at Château Morrisette, one of Virginia's largest wineries, or grab wood-fired pizza and craft beer at Dogtown Pizza. Morning coffee comes from Red Rooster Coffee, artisan-roasted in small batches one block from the only stoplight in town.
Cape Charles
This Victorian-era town on Virginia's Eastern Shore earned Southern Living's nod as the "Best Little Beach Town in Virginia." Once a railroad terminus, Cape Charles fell quiet for decades before a recent revival brought boutiques, restaurants, and vacation rentals to its brick-lined Mason Avenue. The free public beach on the Chesapeake Bay draws couples for sunsets, gentle waves, and the iconic LOVE sign crafted from oyster shells and kayak parts. Stay at Hotel Cape Charles, steps from the beach, or rent a cottage through local agencies.Hook@Harvey provides fine casual dining with sunset views, while The Shanty serves fresh seafood from its waterfront location. Paddle through the marshes on a kayak tour with SouthEast Expeditions, or combine paddling with wine tasting on their Kayak Winery Tour to Chatham Vineyards& Winery. The historic district boasts one of the largest concentrations of turn-of-the-century buildings on the East Coast.
Culpeper
Poet Walt Whitman described Culpeper as "one of the most pleasant towns in Virginia," and the revitalized downtown along East Davis Street proves him right. This Piedmont gem sits 90 minutes from Washington, D.C., and offers direct Amtrak service for couples who want to leave the car behind. Film lovers will treasure the Library of Congress Packard Campus Theater, a 204-seat Art Deco theater built inside a former Cold War bunker that screens classic and rare films from the nation's audio-visual archives for free on weekends. An organ rises from beneath the stage to accompany silent films. Stay at Fountain Hall, a stately inn within walking distance of downtown, or book one of the renovated historic homes through Let's Go and Stay. Dine at Grass Rootes, a farm-to-table restaurant in a former tobacco warehouse with exposed beams and brick wall. Day-trip to Old House Vineyards, Virginia's first combined winery, brewery, and distillery, or drive 30 minutes to Shenandoah National Park's Thornton Gap entrance for a scenic hike along Skyline Drive.
Chincoteague
Made famous by Marguerite Henry's children's book "Misty of Chincoteague," this Eastern Shore island is home to wild ponies that roam the nearby Chincoteague National Wildlife Refuge. While the annual Pony Swim in late July draws crowds, the island offers year-round romance for couples who love nature and seafood. Chincoteague is famous for the wild ponies that roam the nearby marshes. Couples can book a sunset cruise with Chincoteague Step Through Time Tours to see the horses grazing near the Assateague Lighthouse. Take a boat tour with Captain Dan's Around the Island Tours to spot ponies, dolphins, and bald eagles in their natural habitat. Miss Molly's Inn Bed&Breakfast, a Victorian bed and breakfast, provides bikes for guests to pedal through town and out to Assateague Island's unspoiled beaches. The Museum of Chincoteague Island tells the story of Misty and the island's maritime heritage. After a day of wildlife watching, slurp oysters at a local raw bar or grab homemade ice cream at Island Creamery, where flavors like "Pony Tracks" draw lines out the door. NASA's Wallops Flight Facility occasionally launches rockets visible from the island, adding an unexpected spark to evening stargazing.
Your Next Chapter Starts Here
These nine towns represent just a fraction of Virginia's romantic potential, but they share something in common: each rewards couples who slow down long enough to notice the details. Maybe it is the way afternoon light filters through the stained glass at a historic inn, or the sound of a fiddle drifting from a country store on a Friday night. Perhaps it is sharing a bottle of Virginia wine while watching wild ponies graze at sunset, or holding hands during a carriage ride through streets laid with handmade brick. Retirement opens doors that busy careers kept closed, and these destinations welcome travelers who finally have time to savor a long breakfast, take the scenic route, and stay an extra night just because they can. The best romantic getaways do not require elaborate itineraries or jam-packed schedules. They require presence, curiosity, and a willingness to let a place reveal itself on its own terms. Virginia's small towns excel at creating the conditions for connection, whether you have been together three decades or are just beginning your next adventure together.
