Escape with your loved one on unforgettable Romantic Day Trips from Virginia, where charming small towns, scenic drives, and cozy wineries await. Create cherished memories with beautiful landscapes, intimate dining, and captivating local experiences just a short drive away!
Highlights
Best Time for Romantic Day Trips from Virginia:
- March to May – Spring blooms set the scene for garden strolls, vineyard tastings, and scenic mountain views.
- June to August – Summer offers beach escapes, sunset cruises, and charming countryside drives.
- September to October – Fall foliage and crisp air make for dreamy hikes, orchard visits, and cozy small-town dates.
- November – Quiet roads and golden landscapes perfect for antique shopping, café hopping, and winery tours.
- December to February – Winter brings fireside dining, snowy cabin retreats, and festive charm in historic towns.
1. Charlottesville
Rating: ★★★★★
Explore Charlottesville, a charming central Virginia city nestled in the Blue Ridge Mountains, rich in history, culture, and outdoor adventure year-round.
Recommended For: History buffs, wine lovers, and travelers seeking a mix of heritage, nature, and arts in a vibrant Southern setting.
- Visit Monticello and Highland, historic estates of Presidents Jefferson and Monroe.
- Tour the University of Virginia campus, a UNESCO World Heritage Site.
- Explore Shenandoah National Park for year-round hiking and scenic drives.
- Enjoy a thriving independent music scene and cultural attractions downtown.
- Sip your way through Charlottesville’s many award-winning wineries and breweries.
2. Richmond
Discover Richmond, Virginia's historic capital city, where Revolutionary War history, vibrant arts, and modern culinary flair meet along the scenic James River.
Recommended For: History enthusiasts, art lovers, and urban explorers looking for a cultural getaway with Southern charm.
- Visit St. John's Church, where Patrick Henry delivered his legendary speech in 1775.
- Tour the White House of the Confederacy, now a compelling museum.
- Stroll along the revitalized Canal Walk in the city’s vibrant downtown.
- Attend performances at the stunning Richmond CenterStage performing arts center.
- Dine at top culinary spots like Metzger Bar and Butchery, a local favorite.
3. Williamsburg
Step back in time in Williamsburg, a key site of colonial and Revolutionary War history, where immersive experiences and family fun meet in Virginia’s Historic Triangle.
Recommended For: Families, history buffs, and thrill-seekers looking for a mix of education, entertainment, and local flavor.
- Explore Colonial Williamsburg, a living history museum with costumed interpreters and reenactments.
- Visit nearby Jamestown and Yorktown to complete the Historic Triangle experience.
- Ride major roller coasters like Apollo’s Chariot at Busch Gardens Williamsburg.
- Cool off with water attractions at the seasonal Water Country USA.
- Unwind at the Williamsburg Winery, the largest in Virginia, for tastings and tours.
4. The American Visionary Art Museum
Explore the extraordinary at American Visionary Art Museum, Baltimore’s one-of-a-kind destination dedicated to self-taught and outsider art, located in the vibrant Federal Hill neighborhood.
Recommended For: Art lovers, creative thinkers, and anyone inspired by unconventional, boundary-pushing artistic expression.
- Discover over 4,000 pieces of visionary, intuitive, and outsider art.
- See works by artists like Vanessa German, Nek Chand, and Mr. Imagination.
- Explore rotating exhibits and mechanical creations from London’s Cabaret Mechanical Theater.
- Celebrate marginalized voices and self-expression through grassroots creativity.
- Attend special events like the beloved Flicks From the Hill outdoor film series.
800 Key Hwy, Baltimore, MD 21230, Phone: 410-244-1900
5. Brookside Gardens
Immerse yourself in natural beauty at Brookside Gardens, a stunning 50-acre public display garden nestled in Wheaton Regional Park, designed to dazzle the senses through expertly curated floral landscapes.
Recommended For: Garden lovers, families, and anyone seeking a peaceful escape filled with color, fragrance, and inspiration.
- Stroll through themed gardens including the Rose, Japanese, Azalea, and Children’s Gardens.
- Wander along peaceful walking trails surrounded by seasonal beauty and harmony.
- Admire formal plantings of perennials, yews, maples, and fragrant blooms.
- Explore two year-round conservatories featuring lush, exotic plant displays.
- Learn in the horticultural reference library for gardening tips and botanical knowledge.
1800, Visitors Center, Glenallan Ave, Wheaton, MD 20902, Phone: 301-962-1400
6. Chincoteague and Assateague Islands
Escape to Chincoteague and Assateague Islands, two serene coastal retreats on Virginia’s eastern shore, offering unspoiled beaches, wild ponies, and charming seaside hospitality.
Recommended For: Nature lovers, beachgoers, and couples or families seeking a peaceful getaway with scenic views and outdoor adventure.
- Wander through Chincoteague’s historic downtown for boutique shopping and local dining.
- Explore the Chincoteague National Wildlife Refuge, home to diverse birdlife and wild ponies.
- Drive across Maddox Boulevard to Assateague Island’s scenic national seashore.
- Swim, surf, or kayak along 41,000 acres of protected coastal beauty.
- Relax at cozy inns and bed-and-breakfasts steeped in island charm.
Chincoteague & Assateague Islands, Virginia
7. Clifton
Step into small-town charm in Clifton, a picturesque Northern Virginia gem with historic Victorian architecture, local wine, and scenic river trails just outside Washington, D.C.
Recommended For: History buffs, wine lovers, and travelers seeking a quaint Main Street escape filled with character and community events.
- Stroll through the Clifton VA National Historic District lined with preserved 19th-century homes.
- Visit the Buckley House, where *Sleepless in Seattle* was penned.
- Enjoy tastings at Paradise Springs, Fairfax County’s first production winery.
- Hike the Bull Run-Occoquan Trail for riverfront views and natural beauty.
- Celebrate with locals at the Labor Day Car Show or Candlelight Homes Tour.
Clifton, Virginia
8. Fort Washington
Discover Fort Washington, a historic riverside gem in Prince George’s County, Maryland, preserving the legacy of Washington, D.C.’s original defensive stronghold with scenic views and tranquil trails.
Recommended For: History fans, nature lovers, and D.C.-area visitors seeking a peaceful, educational escape with waterfront vistas.
- Explore the original 1809 military fortress that defended the capital through major U.S. wars.
- Stroll through scenic hiking trails with panoramic views of the Potomac River.
- Learn about the site's role in the War of 1812 and the Civil War through historic exhibits.
- Enjoy a leisurely day in the expansive park, maintained by the National Park Service.
- Visit for free outside of regular hours—open to the public before sunset daily.
Fort Washington, Maryland
9. Gaithersburg
Explore Gaithersburg, a dynamic Montgomery County city blending historic charm, innovation, and family-friendly attractions in the heart of suburban Maryland.
Recommended For: Families, shoppers, and travelers seeking a mix of culture, recreation, and tech-driven energy near the nation’s capital.
- Stroll through Olde Towne’s historic district filled with quaint buildings and small-town vibes.
- Cool off at the Water Park at Bohrer Park during summer’s hottest days.
- Sip craft brews at Elder Pine Brewing and Blending Company’s rustic taphouse.
- Shop at the Washingtonian Center (Rio), a premier retail and dining hub.
- Explore nearby Germantown for strawberry picking, markets, and sports fun at the Maryland SoccerPlex.
Gaithersburg, Maryland
10. Staunton
Staunton is a delightful city in Virginia's Shenandoah Valley, named as one of the United States' Dozen Distinctive Destinations by the National Trust for Historic Preservation. The charming city was the first community in Virginia to receive a Great American Main Street Award, renowned for its unparalleled historic architecture. More than 200 buildings within the city were designed by acclaimed 19th-century architect Thomas Jasper Collins, who was known for its gorgeous Victorian-era architecture. Dozens of unique shops, boutiques, art galleries, and restaurants line the city's downtown district, including the Blackfriars Playhouse, which presents live theatrical performances throughout the year. The Woodrow Wilson Presidential Library and Museum commemorates the birthplace of the American president. Other attractions include the Frontier Culture Museum living history facility and the recently-restored Stonewall Jackson Inn.
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