“Let’s take a drive in the country!” If those words spark tingles of anticipation for discovering gently rolling hills, wide open pastures, and towering forests, Madison County will fulfill your daydreams and deliver even more. 


Verdant and peaceful, Madison recalls the countryside of a hundred years ago. Farmhouses abound with their lowing cows and magnificent horses. Dotted with inns and B&B’s, Madison County is the perfect place to wander, explore, rediscover yourself and reconnect with your loved ones. The town of Madison is the hub that can anchor your adventure.

Due to COVID-19 restrictions, please contact individual businesses before visiting, as these details may change at any time. 


22 miles, approximately 36 minutes

In the town of Madison, a wide and welcoming front porch invites you to explore She She on Main, an upscale consignment shop, where finds can include bejeweled satin gowns, custom jewelry and accessories. The newly-opened toy shop is sure to delight. COVID Note: Childrens’ masks and upscale hand sanitizer/beauty packages are available here. Everyday wear, household décor and more round out the offerings. 

The veteran-owned American eatery Mad Local is just up the street. Enjoy southern food served with a smile. Check out the fried green tomatoes for a tasty starter. The menu features local meats and produce, and wine and beer sourced in and around the county.


Be sure to drop by the Madison County Visitors Center, halfway to your next destination, to get the latest news on events, activities and other happenings in the area.

Detour off VA 231 at Banco and pick up VA 670 to discover a truly delightful artists’ enclave. Possum’s Store (A Curious Place) in Criglersville showcases pottery, stained glass, abstract wood sculpture, and yes, decorative possums, created by local artists and artisans. The bright and airy space in a former life served as the general store, circa 1900. COVID Note: Check the event page for updates on workshops and live music.

About a minute up the road you will come upon Rose River Farm. At Douglas Dear’s fisher’s paradise, crystal clear spring water flowing over a rocky bed provides an ideal environment for trophy trout. Catch and release fly fishing is a fantastic way to pass the day in quiet, pristine surroundings. Private and group lessons are offered for the uninitiated, or to brush up on your skills. For full immersion, book a luxury yurt-style cabin for an overnight stay right on the property. 

Photo Credit: Sam Dean, IG account: @sdeanphotos

Horseback riding, apple picking and hayrides are just a few experiences offered at the expansive Graves Mountain Farm and Lodge. The farm encompasses 1,100 acres of streams, ponds, forests and meadows for hiking and fishing. Rock on the porch and enjoy scenic views or stay as active as you care to be. Horseback rides last from an hour and extend to as long as six. Pick-your-own apples is a great fall adventure. The farm offers 27 different varieties – you will no doubt find a new favorite! 


Winding VA 642 takes you north to Etlan. A LOVEworks sculpture marks the entry to Ducard Vineyards, welcoming you to one of Virginia’s first solar powered wineries. Reserve a table on the back patio and relax with your favorite bottle while enjoying a stunning view of the mountains of Shenandoah National Park. Check their calendar for wine and food pairing events in the barrel room and seated tastings of premium selections and library wines that you can reserve in advance. Ducard is one of the southernmost stops on the Blue Ridge Whisky Wine Loop which you can continue north to explore. 


Or reconnect to VA 231 and take a right, turning south where the road is known as FT Valley Road. On this most scenic byway you’ll find Blue Quartz Winery and Shotwell Run Brewing Company, located at the same address so you can sample wines, beers, and cider all in the same tasting room.

Hotels, Resorts, & Other Lodging


25 miles, approximately 45 minutes

This section of Route 29, known as the Tween Rivers Trail, encompasses many of the highlights of Madison County and beyond. This leg of the journey guides you into the heart of Madison, nestled between the Rapidan and Rappahannock Rivers. 

An abundance of outdoor space, complete with picnic tables and tented areas, make a visit to Bald Top Brewery a pleasant stop. Sample brewer Mike’s array of artisan beers, and let owners Dave and Julie fill you in on details while you enjoy some delicious food from the rotation of local food trucks that have partnered with the brewery. Check their calendar for events and live entertainment.

Hop back onto VA 231 and drive north through town. Early American style hand-crafted furniture is the mainstay at regionally-renowned Clore. The family’s heritage dates back to 1830, and pride in craftsmanship is evident. Durable hardwoods such as cherry, oak and walnut infuse each piece with a strength and spirit not often found in today’s disposable culture. 

An early pioneer of Virginia’s resurgent wine scene, Prince Michel Vineyards is one of the commonwealth’s largest wineries. Winemaker Brad Hanson has been crafting delicious quaffs here for over two decades. Brad’s wines have been awarded 400 medals (and counting!) in competition. The tasting room features a large oval bar joined to a glass-walled catwalk that lets you peek into the winery cellar below. Stock up on those necessary - or frivolous - wine accessories found in the gift shop. A further treat for fans of Virginia’s great wines, Prince Michel offers luxurious suites located in the vineyards behind the winery. 

Drive north to Leon and make a right into VA 631 to take the long, meandering way to Spruce Rock Farm. Open from Thanksgiving to Christmas Eve, this family-owned Christmas tree farm offers blue spruce, canaan fir, fraser, concolor fir, and white spruce. Just stop and breathe in the intoxicating scent of evergreens. 

Heading to Revalation Vineyards, resist the urge to spell check: the winery is named for the town of Reva and the grapes have all the regular names: viognier, chardonnay, vidal blanc. Revalation Vineyard is the project of an international couple who fell in love with Madison’s rolling countryside. Julien and Francoise Seillier-Moiseiwitsch carefully planned and developed their farm over a decade. Only opening in 2018, the experimental vineyards were refined to focus on the best-producing red and white vines. A tin-roofed log cabin reclaimed from a farm further south serves to ground a delightful tasting experience. COVID Note: Reservations required. 


If you’re looking for additional spots to eat along this route, dine at Prince Michel Vineyards or Tap 29 Brewery, which has a pub-style menu and plenty of outdoor seating.

Hotels, Resorts, & Other Lodging


20 miles, 30 minutes

Just outside the town of Madison, farmers and artisans ply their trades. Head south on VA 287. At Madison County Farmers Market, their motto is “Eating local means better taste and supporting family farms.” All the folks selling at the market actually live here, and grow the food only minutes away. From just-picked vegetables to eggs, poultry, meat, wine and beer, taste the freshest that Madison has to offer. COVID Note: Currently, you must preorder and pick-up. 

A hidden gem in the same vein is Madison Gardens, just five minutes down the road. In addition to farm-fresh produce, you’ll find a sweet selection of plants and flowers. 

Mennonite baked goods have a justifiably stellar reputation. Somehow the family-made, simple recipes yield the most delicious hand-held fry pies, shoofly pie, and German chocolate cupcakes which is why Yoder’s Country Market is a fine place to replenish while roaming the backroads. Get lunch at the counter and enjoy at the outdoor picnic tables crafted by Amish and Mennonite artisans. Visit the petting zoo too, kids or no kids. 


Wolftown Road leads west to another exciting destination. Early Mountain Vineyards’ grand lodge atmosphere melds seamlessly with their casually sophisticated wines. A certain luxury and ease pervade the place, owing perhaps to the touch of owners Jean and Steve Case of AOL fame/fortune. Honored with the commonwealth’s highest award in 2019 for their Eluvium red blend, Jean Case is an advocate for all the fine wines of Virginia, which she features in her tasting bar alongside Early Mountain’s own. 

Photo Credit: Todd Wright, IG account: @toddwrightphoto

Returning east to VA 29, head south to find quite an astounding assortment of finds. Most unexpectedly, bratwurst, weisswurst (served by folks in drindl skirts and lederhosen) surprise and delight at the Bavarian Chef. A Madison mainstay since 1974, the restaurant serves up the best wiener schnitzel this side of the Danube. COVID Note: Take-out as well as onsite dining are on offer. 

You’ll encounter comfortable log cabin décor at Plow & Hearth, the brick and mortar (so to speak) home of the national retail catalog that overflows with warm flannel sheet sets, wrought iron fireplace tools, hummingbird feeders – all you need to recreate your mountain hideaway fantasies. 

Then round out your dreams with original artwork from MAD Arts (Madison Arts Exchange), a shop you can browse endlessly. Over 200 local artisans show all sorts of one of a kind items in the charming two-story house where room unfolds into room unfolds into room. 


Make the next u-turn and head back north on VA 29 to find – the largest display of outdoor water fountains in the state at Southern Grace. Explore the eclectic garden pieces and home décor under towering trees. Call ahead, you may need an appointment. 

Mosey off the beaten path - slightly north and to the east - and make your way through more gorgeous countryside to The Inn and Tavern at Meander. The epitome of Southern hospitality and elegance, Meander’s 1700’s inn and restaurant display the charm of a different era. Formal gardens are frequented by hummingbirds, tea can be had while rocking on the expansive porch. While Washington may not have slept here, frequent visitors in the past include Thomas Jefferson and the Marquis de Lafayette. 

Photo Credit: M.A.P Drones

Hotels, Resorts, & Other Lodging


Shenandoah National Park extends 70 miles along the skyline of the scenic Blue Ridge Mountains. Madison County is home to two of the park’s most popular attractions. 

Photo Credit: Cameron Davidson

You can park in Nethers near the end of SR 601, at the base of Old Rag Mountain. It’s a five-mile hike to the 3,284 ft. summit where you’ll be amazed by the 360 degree view. For the more adventurous, there’s a 9-mile circuit trail that involves a significant bit of rock climbing over the ancient granite.

White Oak Canyon Trail exhibits a dazzling display of no fewer than six waterfalls, tallest of which is 86 feet. Pack your hiking boots – and your bathing suit – for this excursion. Swimming holes at the base of the falls will serve to refresh!

Photo Credit: Aaron Watson @aaronwatsonphotography

Continue on your WanderLove way by venturing south into Orange County and discover more expressions of Virginia’s LOVE signs nestled into scenic byways.