Chatham VineyardsAutumn 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 three fall destinations that are simply perfect for a romantic weekend in Virginia.


Most people think of the Eastern Shore as a great summertime destination—which it is. 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!

The Eastern Shore is one of the last places in Virginia where the leaves turn, 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 small town coastal Virginia.

Shore residents have also created November Wine & Brine Month, which is a month-long 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.

chatham vineyards. photo credit: Rachel Stevens

Stay at the small-town chic Hotel Cape Charles, a modern hotel on charming and historic Mason Avenue. Or, spend your time at one of the many adorable and romantic bed & breakfasts dotted around Cape Charles, Onancock, and Chincoteague.
This is a Virginia treasure you don’t want to miss.


Scenic Loudoun County. photo credit: Bruce Beddow

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

Visit Loudoun put it best with a winery itinerary to soak in the Loudoun County wine scene:

Begin your day in Virginia’s second smallest town, Hillsboro. Just outside of town, Hillsborough Winery, Brewery & Vineyard is perched along a mountain slope. The tasting room is housed in a renovated 1840s stone barn, a cool respite during the dog days of summer and cozy by the fireplace in winter. From the terrace outside, visitors experience Hillsborough’s luxuriant gardens and trickling fountains, framing the view of the Loudoun Valleys below and the Blue Ridge Mountains in the distance.

breaux vineyards. photo credit: Steven Morris

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. Proceed up the meandering driveway past manicured lawns that give way to sweeping views of vineyards as they extend up Short Hill Mountain. Nestled between the hills, Breaux’s vineyard and mountain views can be enjoyed from the tasting room, Patio Madeleine, 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’ 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. The winery takes advantage of the views, offering numerous seating areas both indoors and out for guests to linger over the scenery and enjoy an overview of Northern Virginia’s Wine Country.

photo courtesy of Salamander Resort

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 seasonal cooking classes with Executive Pastry Chef Jason Reaves on Saturdays, and learn to how to make “Fall Harvest Sweets” using locally harvested ingredients including apples, pumpkins, and raspberries.

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


Golden Eagle Treehouse at Primland Resort. photo courtesy of Primland, Auberge Resorts Collection

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.

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.


Photo Credit: Kenton Steryous

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.

Chateau Morrisette is a beautiful and relaxing experience for anyone who enjoys fine wine, good food, and natural surroundings. You two can tour the unique timber frame winery and spend the afternoon enjoying wine tastings, innovative cuisine, and seasonal events.

Indulge in an experience like none other and stay overnight at the incomparable Primland, Auberge Resorts 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.