Things to Do Near Old Rag Mountain

View from the rocks of Old Rag Mountain over the Shenandoah valley

Things to do near Old Rag and Shenandoah National Park

 

Hiking, sightseeing, food and drink around Old Rag and Shenandoah National Park

Here are some of the places to visit nearby. Our guide gives you an idea of the range of activities, and helps you choose the destinations that best align with your personal interests.

Hiking

 
Old Rag Mountain

Old Rag Mountain

Madison County, Virginia

Under a fifteen-minute walk from Trailside and Foothills, or under fifteen minutes’ drive from Overlook. The circuit is 9.4 miles with 2,348 feet of climbing, around seven and a half hours, and the Park Service rates it very strenuous. You climb the Ridge Trail across the mile-long rock scramble and come down the Saddle Trail and Weakley Hollow fire road — the scramble is not a way down. To skip the scramble altogether, walk up from Berry Hollow on the far side. A day-use ticket is required from 1 March to 30 November, and pets are not allowed on the Ridge, Saddle or Ridge Access trails.

Nicholson Hollow Trail

Nicholson Hollow Trail

Luray, VA 22835, United States

+1 540-999-3500

A fifteen-minute walk from Trailside and Foothills, straight into Shenandoah National Park. The trail follows the Hughes River through the woods, gently at first, with swimming holes along the way — walk in as far as you like and turn back. Carrying on to Corbin Cabin and back is 8 miles with 1,240 feet of climbing, which the Park Service rates moderately strenuous, and the trail runs 5.8 miles in all up to Skyline Drive. River crossings can run knee-deep after heavy rain.

The White Oak Canyon Trail

The White Oak Canyon Trail

Central District

About 20 to 25 minutes’ drive to the lower parking lot. Waterfalls, natural rock slides and swimming pools. From the lower lot the first slide is an easy twenty minutes up the trail, and with children allow another forty-five minutes of steeper climbing to reach the second, much bigger one. The lower falls are a 2-mile round trip with 500 feet of climbing, about an hour and a half, rated easiest. The upper falls are really a separate hike from the top — the Park Service’s 4.6-mile route starts from Skyline Drive at mile 42.6, not from the lower lot.

Little Devils Stairs

Little Devils Stairs

Keyser Run Road (Route 614), near Sperryville, VA

+1 540-999-3500

A 5.5-mile loop with about 1,490 feet of climbing, rated strenuous, from the lower trailhead at the end of Keyser Run Road (Route 614), off Gidbrown Hollow Road north of Sperryville. You climb the gorge beside the cascades on the blue-blazed trail, pass an old family cemetery, then come back down the quieter Keyser Run fire road. A good alternative to Old Rag for anyone not ready for the scramble. The Park Service’s own 7.4-mile version of this loop starts from the top, on Skyline Drive.

Hawksbill Loop

Hawksbill Loop

2.9-mile circuit with 860 feet of climbing, about two hours, rated moderate, from the Hawksbill Gap parking area on Skyline Drive at mile 45.5 — so a drive up, and park entry. It climbs to the highest point in Shenandoah National Park, where a stone viewing platform opens out to a 360-degree view over the Shenandoah Valley, the Blue Ridge and the Piedmont.

Stony Man

Stony Man

1.6 miles there and back, 340 feet of climbing, about an hour, and the Park Service rates it easiest. From the Stony Man parking area on Skyline Drive at mile 41.7. The shortest route to a big view in the park: a rocky summit looking out over the Shenandoah Valley and Massanutten Mountain.

Happy Camper Equipment Co

Happy Camper Equipment Co

An outfitter on Lee Highway in Sperryville, and the place to go for whatever you left at home: boots and trail shoes, packs, rain layers, socks, water bottles. They also stock fly fishing gear, run a thirty-day trial on shoes and a used-gear exchange, and publish their own trail guides. Open 10–5, closed Wednesdays. They shut at the end of December and reopen in early spring — as they put it, when the redbuds flower.

Activities

 
Disc Golf/Hoover Ridge

Disc Golf/Hoover Ridge

158 Primary School Drive Madison, VA 22727

(540) 308‑1247

Eighteen holes laid out across the whole of Hoover Ridge Park and free to play, with the first tee just behind the Carpenter Pavilion near the entrance and parking alongside it. A mix of open ground and woodland, around 5,800 feet, par 58, and well thought of — it rates 4.3 on UDisc. The park runs to over a hundred acres, with playing fields, a pond you can fish with a Virginia licence, a walking trail and a driving range, so it holds an afternoon even if only half the party plays.

The Schoolhouse Nine

The Schoolhouse Nine

12018 Lee Highway, Sperryville, VA 22740

(540) 987‑5008

Rappahannock County’s only golf course, and an unusually pretty one: nine holes, par three, with tee shots from 85 to 170 yards, winding through native wildflower meadows beside the Thornton River. The old red schoolhouse serves as the clubhouse, and it is the same complex that houses Happy Camper, so clubs and trail shoes are a single stop. Short, inexpensive and forgiving enough for beginners and children.

Jenkins Mountain Disc Golf, near Old Rag and Shenandoah National Park

Jenkins Mountain Disc Golf

72 Christmas Tree Ln, Washington, VA

Eighteen holes over 55 acres of woodland and hill pasture at Little Washington Winery, with a brewery and a winery on the same site — by their own account the only disc golf course in the world that can claim both. Lots of elevation, wide views over the Blue Ridge, and a thoroughly unhurried afternoon whether or not anyone keeps score.

Horseback riding at Graves Mountain

Horseback riding at Graves Mountain

Guided trail rides from the farm at Syria, across their own land and up into the national park. Rides go at a walk whatever your experience, helmets are provided and required, and riders need to be at least eight years old and 54 inches tall. Times and prices shift with the season, so check with the farm before you drive over.

Sightseeing

 
Skyline Drive

Skyline Drive

The road that runs the length of Shenandoah National Park, 105 miles from Front Royal to Waynesboro along the crest of the Blue Ridge, with overlooks most of the way. The speed limit is 35 mph and the full run takes about three hours. Of the four entrance stations, Thornton Gap above Sperryville is the closest to us, about a twenty-five minute drive from the houses. Weather can close the road at any time.

Luray Caverns

Luray Caverns

101 Cave Hill Rd, Luray, VA 22835, United States

+1 540-743-6551

One of the largest cavern systems in the eastern United States, and the one most people mean when they say they are going to see the caves. Vast lit chambers of stalactites and stalagmites on a paved route, about an hour with a guide, and the Great Stalacpipe Organ, which is exactly as odd as it sounds. Easy with children, and a good answer to a wet afternoon.

Sperryville

Sperryville

Rappahannock County, Virginia, United States

Nestled within the embrace of the Blue Ridge Mountains, Sperryville is a picturesque town where historic charm meets natural beauty. Wander through local artisan shops offering handmade crafts, explore cozy cafes, and immerse yourself in the town’s vibrant culture.

Monticello

Monticello

1050 Monticello Loop, Charlottesville, VA 22902, United States

+1 434-984-9800

Step into history at Monticello, the remarkable estate of Thomas Jefferson. Tour the iconic home, meticulously designed by Jefferson himself, and wander through its sprawling gardens boasting diverse flora. Delve into the complexities of American history while experiencing the legacy of one of its most influential figures.

James Madison’s Montpelier

James Madison’s Montpelier

11350 Constitution Hwy, Montpelier Station, VA 22957, United States

+1 540-672-2728

Embark on a journey through the life of President James Madison at Montpelier, his former plantation home. Immerse yourself in history as you tour the estate, gaining insights into Madison’s significant contributions and the historical heritage that shaped the nation.

Madison

Madison

Madison, Virginia, United States

The county seat, and the nearest town of any size on the southern side. A short Main Street of old storefronts with cafés and places to eat, a public library, and a farmers market at the fairgrounds on Saturday mornings in season. Useful for supplies, and pleasant enough to linger in.

Fishing/Tubing

 

Trailside & Foothills: The Hughes River is located directly across the street from these properties, with excellent fishing access within a short 10-minute walk. Virginia actively stocks the Hughes River with trout, along with two other nearby rivers.

Overlook (Etlan): Located in beautiful Etlan, Overlook is situated in a premier trout-fishing corridor. Guests are just a short drive from some of Virginia’s best trout water, from the stocked runs of the Rose, Robinson and Hazel to the world-class native brook trout of the upper Rapidan.

For walk-and-wade access there are small roadside pull-offs: the Hughes runs beside Nethers Road, the Robinson along Bohannon Road, and the Rose near the Old Blue Ridge Turnpike in Syria. The Hazel takes a walk in from the park rather than a pull-off. These lower stretches are mostly stocked water and often run alongside private land, so watch for Posted signs and keep to the public sections — the wild native brook trout are further up, inside the park. The upper Rapidan is reached from Graves Mill, and the Conway River, on the Greene county line beside the Rapidan Wildlife Management Area, holds both brook and brown trout.

If you would rather fish still water, or have children who want to actually catch something, Lake Orange is a quiet 124-acre DWR-managed lake with a floating fishing pier and seasonal boat rentals. In Culpeper, Mountain Run Lake and Lake Culpeper (formerly Lake Pelham) offer shore fishing and boat ramps for largemouth bass, bluegill and crappie, and Lake Culpeper also has yellow perch. Lake Culpeper is electric motors only.

Tubing: the rivers on our doorstep are for fishing and wading rather than floating. For tubing proper the Shenandoah is the one, where outfitters run float trips from a couple of hours to most of a day and shuttle you back to your car. It is a drive rather than a stroll from the door, but on a hot afternoon in July nobody minds.

If you would rather paddle than float, the Town of Culpeper rents canoes, kayaks, paddle boards and paddle boats at Lake Culpeper Adventures, beside The Ole Country Store on Route 29 south. It is first come, first served with no reservations, the hirer needs to be eighteen with photo ID, and life jackets come with the boat. The season runs through the warmer months and can end early in a dry year, so ring ahead outside high summer.

Two sets of rules worth knowing before you set off: the upper Rapidan is catch-and-release, and the Conway is special-regulation water — single-hook artificial lures only, no bait, a nine-inch minimum and six fish a day.

Fishing seasons, trout stocking, licenses and regulations are available on the Virginia DWR website.

If you would rather go out with someone who knows the water, Happy Camper in Sperryville recommends three local fly fishing guides: Brett Elford (818-825-7905), Page Valley Fly Fishing Service and Dragon Fly Fishing Company. The recommendation is theirs rather than ours — we have no connection with any of them.

Many rivers nearby offer fishing for trout and other species

Many rivers nearby offer fishing for trout and other species

Shenandoah National Park contains over 90 mountain streams and their minor tributaries that serve as high quality sources for three of Virginia’s ten major drainages: Potomac, Rappahannock, and James.

Seven Bends State Park (North Fork Shenandoah River)

Seven Bends State Park (North Fork Shenandoah River)

2111 S. Hollingsworth Road, Woodstock, Shenandoah County, VA 22664

1‑800‑933‑7275

Situated near Woodstock in the unique “Seven Bends” area of the North Fork Shenandoah River, this 1,066‑acre state park includes public river access for wade and float fishing, picnicking, and exploring trails along the riverbanks. Smallmouth, sunfish, and other species are common in riffle and ledge habitats

Shenandoah River Outfitters

Shenandoah River Outfitters

6502 S Page Valley Rd, Luray, VA 22835, United States

+1 540-743-4159

Plan a family-friendly river adventure with a raft rental from Shenandoah River Outfitters. Glide through the warm, shallow waters and soak in the scenic beauty while enjoying a leisurely journey downstream.

Shenandoah River State Park (Raymond R. “Andy” Guest Jr. State Park)

Shenandoah River State Park (Raymond R. “Andy” Guest Jr. State Park)

350 Daughter of Stars Drive, Bentonville, VA 22610

(540) 622‑6840

A 1,600‑acre park along the scenic South Fork of the Shenandoah River offering excellent fishing for smallmouth and largemouth bass, sunfish, catfish, and seasonal float trips. Trails and river frontage offer access and peaceful scenery

Restaurants and cafes

 
The Everybody Eats counter at New Iberia Kitchen, Sperryville, Virginia

New Iberia Kitchen

3 River Ln SPC 9, Sperryville, VA 22740

+1 540-227-6647

Savor a unique culinary adventure at New Iberia Kitchen, where American comfort food gets a vibrant Louisiana and Spanish twist. Located right inside The Marketplace, it’s the perfect spot to gather with friends, enjoy a warm, casual atmosphere, and explore rich, deeply flavorful dishes rooted in heritage.

Cake Krums Cafe

Cake Krums Cafe

117 N Main St, Madison, VA 22727

+1 540-543-3451

An adorable local treasure nestled right in the heart of historic Madison. It is the ultimate cozy retreat to unwind over spectacular specialty espresso drinks, loose-leaf teas, and mouthwatering, freshly baked homemade pastries.

Blue Rock

Blue Rock

12567 Lee Hwy, Washington, VA 22747

(540)987-3388

Blue Rock has a restaurant for special occasions and a bar serving more informal fare. Both offer indoor and outdoor seating, and lovely views to go with your meal.

Rappahannock Pizza Kitchen on Main Street, Sperryville, Virginia

Rappahannock Pizza Kitchen (RPK)

3710 Sperryville Pike, Sperryville, VA 22740, United States

+1 540-987-9494

Indulge in flavorful pizzas and local favorites at Rappahannock Pizza Kitchen. With a carefully curated menu and the option to customize your pie, it’s a delightful dining experience complemented by their inviting outdoor space.

The Inn at Little Washington

The Inn at Little Washington

309 Middle St, Washington, VA 22747, United States

+15406753800

Enjoy a luxurious dining experience with gourmet dishes prepared by acclaimed Chef Patrick O’Connell.

Three Blacksmiths

Three Blacksmiths

20 Main St, Sperryville, VA 22740, United States

+1 540-987-5105

Secure your reservations ahead to relish the culinary artistry at Three Blacksmiths, an upscale dining destination known for its meticulously crafted menu and sophisticated ambiance.

Los Brothers Restaurant, near Old Rag and Shenandoah National Park

Los Brothers Restaurant

217 N Main St, Madison, VA 22727

Mexican cooking on Madison’s Main Street, generous and unfussy, and the kind of place a family can turn up at after a long day on the mountain without booking.

Before & After, near Old Rag and Shenandoah National Park

Before & After

31 Main St, Sperryville, VA 22740

+1 540-683-5333

A small coffee shop on Sperryville’s Main Street doing proper coffee alongside sandwiches, pastries and a chicken salad people make a point of mentioning. Open 8am to 3pm daily — the obvious stop on the way to the trailhead.

Off The Grid, near Old Rag and Shenandoah National Park

Off The Grid

11692 Lee Hwy, Sperryville, VA 22740

+1 540-987-5114

Mediterranean food in an informal room in Sperryville: naan, hummus, salads and grills. Open from mid-morning to five, and closed Wednesdays and Thursdays, so check before you set off.

Patty O’s Café & Bakery, near Old Rag and Shenandoah National Park

Patty O’s Café & Bakery

389 Main St, Washington, VA 22747

+1 540-675-3801

The relaxed end of Little Washington’s dining, from the same stable as the Inn: a bakery and café serving lunch and dinner without the occasion or the price tag. Popular evenings get tight, so go early or late.

Wineries and breweries

 
DuCard Vineyards

DuCard Vineyards

40 Gibson Hollow Ln., Etlan, VA 22719

(540) 923-4206

Escape to a peaceful mountainside sanctuary at DuCard Vineyards, a boutique winery tucked away at the very edge of Shenandoah National Park and a short drive away from our homes. Sip on gold-medal-winning, estate-grown wines while relaxing on the patio beside a babbling stream, all set against the breathtaking backdrop of Old Rag Mountain. They are also the only winery nearby open seven days a week, year round, though hours shift with the season and around holidays, so it is worth checking before you set out. Guests of Old Rag Escapes get a two-for-one tasting flight, one per reservation.

Copper Fox Distillery

Copper Fox Distillery

9 River Ln, Sperryville, VA 22740, United States

+1 540-987-8554

Embark on an immersive whisky-tasting journey at Copper Fox Distillery. Discover an array of exquisite selections and dive into the rich tradition and craftsmanship behind each sip.

Hopkins Ordinary Aleworks

Hopkins Ordinary Aleworks

47 Main St, Sperryville, VA 22740, United States

+1 540-987-3383

An outdoor beer garden on Main Street in Sperryville, pouring their own craft brews in a walled garden behind a historic building. A good place to end a day on the mountain.

Pen Druid Brewing

Pen Druid Brewing

3863 Sperryville Pike, Sperryville, VA 22740, United States

Experience the artistry of wild-fermented beers against the backdrop of panoramic mountain views at Pen Druid Brewing. Celebrated for its unique brewing techniques and terroir-driven approach, this brewery captures the essence of local flavors in every sip.

Blue Quartz Winery, near Old Rag and Shenandoah National Park

Blue Quartz Winery

Route 231, Madison County, VA

Estate-grown wine, hard cider and craft beer under one roof on Route 231 — the tasting room is shared with Shotwell Run Brewing, so the wine drinkers and the beer drinkers in your party can stop arguing. Food from the kitchen and grill, or the food trucks on site.

Sharp Rock Vineyards, near Old Rag and Shenandoah National Park

Sharp Rock Vineyards

5 Sharp Rock Road, Nethers, VA 22740

The nearest vineyard to Old Rag Trailside and Old Rag Foothills, at the junction of Nethers and Sharp Rock Roads, a few minutes from the door. A small family vineyard in a converted farmhouse, with the mountain itself filling the view from the tasting room.

Festivals and markets

 
The rubber duck race on the Thornton River at SperryFest, Sperryville, Virginia

SperryFest

Main Street and the Schoolhouse Field, Sperryville

One Saturday in late April

Sperryville’s big day out. Forty-odd artisan vendors, food trucks and music along Main Street, and the Great Rubber Duck Race on the Thornton River. Attendance and parking are free. Fifteen minutes from Old Rag Trailside and Old Rag Foothills.

Rappahannock County Farm Tour banner, last full weekend in September

Rappahannock County Farm Tour

Farms across Rappahannock County

The last weekend in September

A free, self-guided tour over two days, with around a dozen farms and vineyards opening their gates. You drive between them at your own pace. The best two days of the year for seeing how this valley actually works.

Graves Mountain Apple Harvest Festival, near Old Rag and Shenandoah National Park

Graves Mountain Apple Harvest Festival

Graves Mountain Farm & Lodges, Syria

The first three weekends in October

Apple picking, cider, music and barbecue on the farm at Syria, across the first three weekends of October. It is the closest of these to Old Rag Overlook, a few minutes up the road. Go early in the day if you can.

Taste of the Mountains, near Old Rag and Shenandoah National Park

Taste of the Mountains

Main Street, Madison

The Saturday of Labor Day weekend

Madison gives over Main Street to a street festival of crafts, music, food and pony rides, run by the county chamber of commerce. Twenty minutes from the houses, and the last big weekend of the summer.

Rappahannock County Farmers Market, near Old Rag and Shenandoah National Park

Rappahannock County Farmers Market

The Schoolhouse lawn, Sperryville

Saturdays 9am to noon, April to November

Produce, bread, meat, flowers and cheese from farms within a few miles of the stall. Worth building a Saturday morning around if you are planning to cook at the house.

Madison County Farmers Market, near Old Rag and Shenandoah National Park

Madison County Farmers Market

Fairground Road, Madison

Saturday mornings in season

The Madison side’s market, on Saturday mornings at the fairgrounds. Smaller than Sperryville’s, and the more convenient of the two if you are staying at Old Rag Overlook.

Shopping

 
The F.T. Valley Farm at Mont Medi sign on Route 231, Sperryville, Virginia

F.T. Valley Farm

513 F.T. Valley Road, Sperryville, VA 22740, United States

+1 540-351-9156

A family-owned orchard and farm market on a Virginia Scenic Byway, with fresh apples, grass-fed beef, hard cider, cider donuts, local cheeses and artisan goods, plus seasonal cut flowers and live music events.

Roy and Janet’s Orchard and Farm Store near Sperryville, Virginia

Roy’s Farm Market

64 Old Hollow Rd, Sperryville, VA 22740, United States

+1 540-987-8636

Located about 17 minutes from the houses, Roy’s Farm Market offers a true taste of local produce. This old-fashioned farm market has a well-rounded selection, from seasonal fruits and vegetables to ice cream, meats, and staples. You can also enjoy giant marshmallows, ice cream sandwiches, homemade pies, and even pick cherries and blueberries when in season, all in a charming, low-key setting. Cards and Apple Pay accepted. Open Mon-Sun 8am-8pm. Watch for the turning: the sign on the road reads Roy & Janet’s Orchard & Farm Store, which is the same place.

The Little Country Store

The Little Country Store

5338 S F T Valley Rd, Etlan, VA 22719, United States

+1 540-683-8004

Get pulled pork sandwiches and discover locally sourced meats for grilling. Just a short drive from the houses, it’s a convenient stop for basic items .

The Corner Store on Main Street, Sperryville, Virginia, trading since 1859

The Corner Store

3710 Sperryville Pike, Sperryville, VA 22740, United States

+1 540-987-8185

A proper village shop, trading on Main Street since 1859 and sharing its address with the pizza kitchen next door. Fresh meat, beer and wine, and the groceries you meant to bring. The most useful stop in Sperryville if you are cooking at the house, and worth the trip even for one forgotten thing.

Jenkins Orchards

Jenkins Orchards

355 Yancy Rd, Woodville, VA 22749, United States

+1 540-987-8192

Explore the bounty of fresh, locally sourced produce and fruits at Jenkins Orchards.

Yoders Country Market

Yoder’s Country Market

2105 S Seminole Trail, Madison, VA 22727, USA

+1 540-948-3000

Embark on a culinary treasure hunt at Yoder’s Country Market, offering an array of baking ingredients and a diverse selection of groceries for all your culinary needs.

Bean Hollow Grassfed

Bean Hollow Grassfed

15 A Over Jordan Farm Ln, Flint Hill, VA 22627, United States

+15406751025

Bean Hollow Grassfed is a family-owned farm specializing in high-quality, grass-fed beef and lamb in central Virginia.

Waterpenny Farm

Waterpenny Farm

53 Waterpenny Ln, Sperryville, VA 22740, United States

+1 540-987-8567

Indulge in organic produce grown without pesticides at Waterpenny Farm’s stand, open daily to cater to your fresh ingredient requirements.