Fall Destinations for a Romantic Weekend Getaway

Autumn in Virginia is one of the most romantic times of year. The weather is crisp and cool and the fall foliage is breathtaking. Virginia also boasts activities like hiking, apple picking, and wine tasting, which makes it the perfect destination for a romantic weekend getaway.

Whether you want to curl up by the fire in a cozy mountain cabin, or cast your gaze on an autumn sunset over the Chesapeake Bay, Virginia is the perfect place to plan a 48-hour escape with your main squeeze. Here are some favorite fall destinations that are simply perfect for a romantic weekend in Virginia.
 

Jump to: Northern Virginia Getaways | Mountain Escapes | Central Virginia Trips
 

ENJOY A FALL SEASIDE GETAWAY

Coastal destinations are the last to change colors in the state, meaning you can enjoy fall foliage late into the season. Take romantic sunrise strolls on the beach, shop local at many of the boutiques and specialty shops around the area, and enjoy the peace and quiet of a small coastal town or an iconic beach destination during the slow season.

Eastern Shore

The Eastern Shore is a prime destination for summer getaways. But we’re going to let you in on a little secret — the Eastern Shore is a hidden gem for autumn travel, and will be a perennial favorite once you’ve visited in the fall!

Check in to the small-town chic Hotel Cape Charles, a modern hotel on charming and historic Mason Avenue. Spend your day strolling around the shops, art galleries, and restaurants and be sure to stop by Brown Dog ice cream and the cozy and romantic Cape Charles Distillery. Or, spend your time at one of the many adorable and romantic bed & breakfasts dotted around Cape Charles, Onancock, and Chincoteague.

Shore residents have also created Eastern Shore Wine & Brine, which is an autumnal celebration of Virginia oysters and wine. November is the month to officially celebrate the Eastern Shore’s distinct viticulture and aquaculture offerings, and tout the hyper-local benefits of growing grapes within steps of some of the best aqua farming in the country. A full calendar of events includes traditional Shore oyster roasts, wine & oyster festivals, wine dinners, and raw bar tastings. Be sure to pop by Chatham Vineyards, Virginia’s only Eastern Shore winery.

This is a Virginia treasure you don’t want to miss.

Virginia Beach

A busy summertime destination, Virginia Beach takes a nice, quiet turn in the fall. Still rife with amazing restaurants, shops, and fun things to do, the off-season provides a slower pace and the ability to enjoy everything the area has to offer with less crowds.

For the ultimate romantic stay, consider The Historic Cavalier Hotel and Beach Club. If you are planning an early season visit, you might be able to spend some time at the Beach Club before it closes for the season, usually in October, weather-dependent. If not, there are still plenty of romantic options on site, like the hotel’s luxurious spa, stunning indoor pool and hot tub, cozy romantic whiskey bar, and on-site distillery.

Take a romantic walk on the boardwalk without the crowds, pop by a local brewery, or head to one of the city's amazing restaurants. We recommend Lovesong for funky vibes and unique farm-to-table eats or Orion's Roof for the best views in the area.

A SLICE OF HISTORY WITH A SIDE OF WINE

The options are endless in Northern Virginia, from a historic city with cobblestone streets, romantic restaurants, and waterfront views to one of the state’s most award-winning wine regions. You are bound to find your perfect romantic fall weekend here.

Loudoun County 

Located just 25 miles from our nation’s capital, Loudoun County is Northern Virginia’s premiere destination for wine lovers. Boasting 50+ wineries and tasting rooms, this is the perfect destination for oenophiles. Loudoun also has the LoCo Ale Trail, featuring over 30 breweries, for those who lean more towards suds over sipping wine.

Located on the historic Boxwood Estate, Boxwood Winery offers a beautifully designed tasting room and serene outdoor spaces — the perfect backdrop for a romantic afternoon. Travel northwest from Hillsboro to Breaux Vineyards, one of Virginia’s largest wineries, with over 100 acres of vineyard planted across their 404 acre estate. Nestled between the hills, Breaux’s vineyard and mountain views can be enjoyed from the tasting room and their landscaped terraces.

End your day with one of the most impressive views in the county. Bluemont Vineyards sits high on an eastern slope of the Blue Ridge Mountains at 951 feet above sea level, offering spectacular views of the countryside and beyond. It’s said that on a clear day, you can even see the Washington Monument from the tasting room.

After a wonderful day of wine tasting, relax and unwind at the luxurious Salamander Resort & Spa in Middleburg. You can take in everything that Virginia’s horse and wine country has to offer at this sprawling resort. Tour the vibrant fall foliage, taste local wines, gather around the fire pits, ride horses, and soar high on their zip lines. You and your sweetie can sign up for a private and unique dining experience at Harrimans Cooking Studio. 

After a weekend in Loudoun County, you and your other half are sure to come home even more in love!

Alexandria

Looking for a charming, historic city with cobblestone streets and small town vibes for your next romantic weekend in Virginia? Alexandria is the perfect place for you and that special someone. The historic buildings in the Old Town neighborhood offer a cozy, romantic setting. If you choose an Old Town hotel, you’ve set yourself up for a nice, walkable weekend.

Morrison House in Virginia exudes romance with its charming blend of historic elegance and modern luxury. The boutique hotel’s intimate atmosphere, luxurious rooms, and personalized service create a perfect setting for a romantic getaway, while its prime location in Old Town Alexandria offers easy access to quaint shops, fine dining, and scenic waterfront strolls.

For a unique spa experience, take your partner to Balian Springs and indulge in a wide array of wellness experiences, from hydrotherapy pools to unique immersive lounges, like infrared, Himalayan salt, and loess saunas. End the day on the rooftop to watch the sun go down in the hot tub with a nice cocktail in hand.

Check out our complete guide to visiting Alexandria for more romantic recommendations. 
 

A DREAMY MOUNTAIN ESCAPE

There’s nothing more romantic than a picturesque drive along the Blue Ridge Parkway in the fall. The vibrant colors, majestic mountains, and miles of scenic roads are enough to make anyone swoon. So, grab your honey’s hand and treat yourself to a mountain escape in beautiful, rustic Southwest Virginia.

Floyd

Venture to Floyd, located in the Blue Ridge Highlands region of Virginia. Bordered on the southeast by the Blue Ridge Parkway, Floyd is a small mountain town boasting music, art, and wine. Be sure to stop by the Floyd Country Store for its Friday Night Jamboree and learn to two-step with your partner.

Visitors to Floyd quickly find that music is the town's heartbeat. Old-time fiddlers, bluegrass banjo pickers, blues guitarists, African drummers, and jazz cats collectively make this place a music lover's dream.

Nicewonder Farm & Vineyards

Nestled in Virginia’s blue ridge mountains, Nicewonder Farm & Vineyards offers a picturesque escape for couples seeking romance and tranquility. The charming property features rolling vineyards, charming private yurts, and elegantly appointed accommodations. From the moment you arrive, you’re greeted with stunning views and an atmosphere of serene elegance, perfect for unwinding and reconnecting.

Enhance your stay with a private wine tasting of estate-grown vintages, or enjoy a romantic dinner at the on-site restaurant, Hickory, where farm-to-table cuisine meets gourmet flair. Don’t miss the newly added spa offering innovative treatments for some ultimate relaxation. If you’re looking for a little adventure, head over to downtown Bristol for some live music or antique shopping.

The Lodge at Primland, Auberge Collection

Indulge in an experience like none other and stay overnight at the incomparable The Lodge at Primland, Auberge Collection. Spectacular views, mountain-top chalets, elegant dining, and a wide array of recreational activities await you at this Meadows of Dan jewel. Primland has something for every couple, whatever you enjoy doing together—from getting a couples’ massage to horseback riding, kayaking to nature walks, sporting clays to stargazing, tennis to tree climbing.

Get closer to nature—and each other—at this unrivaled Southwest gem.

WINE LOVERS WEEKEND GETAWAY

For an unforgettable wine lover’s weekend getaway, Central Virginia offers a delightful mix of scenic beauty and world-class wineries.

Charlottesville

Begin your Charlottesville journey at Pollak Vineyards, where you can savor exquisite wines while soaking in the stunning views of the Blue Ridge Mountains on horseback. The estate's serene ambiance and meticulously crafted wines create an idyllic start to your weekend. 

Continue to Pippin Hill Farm & Vineyards, a perfect blend of rustic charm and elegance. Enjoy a wine tasting paired with farm-to-table cuisine on their veranda, overlooking lush vineyards. For a comprehensive wine experience, explore the Nelson 151 trail, home to some of the region's finest wineries and breweries. This trail offers a picturesque route through Virginia’s wine country, making it an ideal destination for wine enthusiasts seeking both relaxation and adventure.

After a day of wine tasting, head to Charlottesville for a memorable dinner. The city boasts a vibrant culinary scene with many restaurants that celebrate local flavors. Enjoy a romantic dinner at Public Fish & Oyster, where you can indulge in fresh, sustainable seafood paired with an extensive wine list. The cozy atmosphere and exceptional service ensure a delightful dining experience, perfectly complementing your wine weekend. Whether you're savoring oysters or a seafood entree, this spot adds a touch of elegance to your Central Virginia getaway.

Stay right down the street at the stunning Doyle Hotel, offering the best scenic views of the area from their rooftop bar. This art-focused hotel is also within walking distance to Charlottesville’s Downtown Mall, where you will find a plethora of fun shops and romantic dining options.

Keep planning your Cville getaway with our complete guide to visiting Charlottesville. 

Keswick & Gordonsville

Just down the road from Charlottesville, you can find another upscale treat for you and your main squeeze. Keswick Hall is a luxury resort offering stunning views, a top-notch spa, golf course and on-site restaurant, Marigold by Jean-Georges. Book yourself a room with a private patio for all the fall foliage views during your stay and be sure to sign up for a romantic couple massage.

During your stay head down the road to one (or all) of the stunning nearby wineries and cideries nestled in the scenic Virginia countryside. Pop into Southwest Mountain Vineyards’ stunning tasting room and get a flight of their award-winning wines. Take in the view from one of their lovely balconies or patios.

Two other nearby wineries not to be missed are Keswick Vineyards and Merrie Mill Farm & Vineyard.

To polish off your adventure, head a little further down the road to Gordonsville for charming small towns fall vibes and the best antique shopping around.