Day Trippin’: So Much to See, So Close to Home

Hunter's Head Tavern as seen from John S. Mosby Highway, with the London-style phone booth as a landmark.

A trek through time and nature, from northern Fauquier’s Sky Meadows to the historic town of Upperville to the food and wine country around Middleburg.

Want the feeling of getting away from it all with the benefits of staying close to home? This all-day rollick across northern Fauquier County and southwestern Loudoun County will do the trick! This route takes you north through the rolling green hills of the Crooked Run Valley to Sky Meadows State Park and the Federal-era village of Upperville, then east along the Mosby Trail through Middleburg into the hilly wine country where Loudoun County meets Prince William. The trip ends back in Fauquier with a visit to an old-fashioned country market. From a rural bakery breakfast to a British pub and back, it’s a gastronome’s dream married to an outdoorsman’s Blue Ridge bucket list, all in under fifty miles.

Red Truck Bakery

8368 W. Main Street, Marshall

Red Truck Bakery granola. Photo courtesy of Brian Noyes, Red Truck Bakery

A special day calls for a special starting point. The picture-perfect Red Truck Bakery in Marshall more than fits the bill. Opened in 2015 following the success of Red Truck’s Warrenton location, the bakery’s pastries, tarts, cakes, and jams have earned it “oohs” and “aahs” from publications like Condé Nast Traveler, Southern Living, and O, The Oprah Magazine. The Marshall bakery, housed in the red brick building that was originally the town’s pharmacy, has an industrial farmhouse feel with retro lighting, long farm tables, and seating for up to 40 patrons.

“If you need a solid breakfast before hiking, we’re your place,” says owner Brian Noyes. Ingredients from Red Truck’s breakfast menu of quiches, muffins, croissants, and pastries include pecans sourced from Rappahannock County, apples from the Shenandoah Valley, and eggs, dairy, chicken, produce, and cheese from nearby farms.

The Travel Channel’s Andrew Zimmern hailed Red Truck’s granola as the best in North America. Grab a bag of granola and some mason jars of Runningbyrd Iced Tea or MTO Kombucha on your way out. They’ll make for an upscale take on old-school hiking grub as you prep for your next stop, Sky Meadows State Park.

Sky Meadows State Park

11012 Edmonds Lane, Delaplane

Sky Meadows State Park Photo courtesy of VA State Parks Staff

Sky Meadows offers 24 miles of interconnected hiking and biking trails and breathtaking scenery. To get there, hop on I-66 west from Marshall, and take exit 23 (Delaplane), then follow US-17 North another 6.4 miles to this 1,900-acre state park in the foothills of extreme northwest Fauquier County. Be sure to bring cash for parking at the typically self-service entrance kiosk. Entrance is $5 per vehicle, except during special events.

Pick up a park trail guide from the kiosk, then decide what you’re willing to tackle. There are options for short jaunts through rolling fields on the lower trails. A highlight is the 20-minute stroll to the ruins of Snowden Manor, a pre-Civil War frame house. The more adventurous might opt for something more tasking, like the steep climb to the sweeping views at Piedmont Overlook, or a longer circuit hike that takes adventurers past Turner Pond to Lost Mountain.

Most hikes emanate from Sky Meadows’ main parking lot. Just beyond this lot is the park’s historic area, which includes visitor facilities, restrooms, a gift shop, a one-and-a-half story log kitchen, and the expansive Mount Bleak House, a Federal-style mansion built in the 1840s.

“Mount Bleak House tours are dependent on volunteer availability,” says Chief Ranger for Visitor Experience Kevin Bowman, but many are scheduled on weekend mornings throughout the summer. In addition, “During the Delaplane Strawberry Festival, the house will be open with volunteers and staff in an open-house format from 11 a.m. – 4 p.m. so that visitors can enjoy at their own pace.” Sky Meadows hosts a number of events in addition to these tours, ranging from star-gazing to cooking demonstrations to Civil War encampments. Check out their schedule at

When you have enjoyed your time here, journey ten minutes north on US-17 from Sky Meadows, then head east on US-50 to reach the small, scenic village of Upperville. Your first stop here is the Hunter’s Head Tavern. You’ll know you’re in the right spot when you see the bright red London-style phone booth just off the tavern’s parking lot.

Hunter’s Head Tavern

9048 John S. Mosby Highway, Upperville

Hunter’s Head is part of Ayrshire Farms, a 1,000-acre Certified Humane ® and USDA Certified Organic farm owned by Cisco co-founder Sandy Lerner. The tavern offers an authentic British gastro-pub experience which demonstrates the farm’s commitment to local, sustainably-farmed meats and produce, including Ayrshire’s own crops and heritage-breed livestock.

Hunter’s Head’s menu is a mix of pub fare (imagine shepherd’s pie, fish and chips, and bangers and mash), and seasonably-available fine dining options like braised short ribs, house-smoked trout, and lemongrass-ginger chicken lettuce wraps. In the unlikely event that you have any room left after your main, check out tavern-favorite Banana Pudding Cake. We won’t tell.

Part of Hunter’s Head’s draw is its cozy environs. The tavern operates out of the Old Carr House, which started life as a log cabin built around 1750 by a Scottish settler of the Virginia frontier. The property was later bought by Joseph Carr, whose general store grew so successful that in 1797 Upperville was first founded as “Carrstown.” Several additions were added to the house over the years, some of which now function as snug dining rooms.

Trinity Episcopal Church

9108 John S. Mosby Highway, Upperville

Trinity Episcopal Church was built in in the 1950s, mostly from native sandstone quarried in Warrenton. Nearly of all its stone and woodwork was done by local craftspeople. The stunning church was built in the style of medieval French churches, and in the tradition of that time, the tradespeople who crafted Trinity made their own tools at a forge on the property.

“The church is open and can be visited any weekday during business hours from 9 a.m. – 4 p.m., as well as for worship on Sunday mornings,” says Parish Administrator Phil Mohr. In addition to the primary church buildings, an antique greenhouse, thrift store, and tiny stone library also sit on Trinity’s stroll-worthy 35-acre campus. The thrift store is open from 9 a.m. – noon on Saturdays. The library, which was constructed around 1804, houses historic documents pertinent to Upperville’s history.

CS Arms, Inc.

9150 John S. Mosby Highway, Upperville

CS Arms feels as much like a military museum as a shop, in part due to the expertise of its genial owner, Cliff Sophia. Sophia carries an amazing array of antique and collectors’ firearms, swords, uniforms, and other militaria. A four-decade student of arms and military history, Sophia has been in the military antiquities business for nearly two decades. The curios for sale here have attracted the likes of the late Senator John Warner. CS Arms is open 10 a.m. – 5 p.m. Tuesday through Saturday.

Goose Creek Stone Bridge

Intersection of John S. Mosby Highway and Lemmons Bottom Road (Route 832)

Goose Creek Bridge
Goose Creek stone bridge is located on Route 832. Sarah Stierch

Five minutes east of Upperville is Goose Creek Stone Bridge. Now located just off of Mosby Highway (US-50 E), this one-time travel hub was a center of intense fighting during the June 21, 1863, Battle of Upperville. It was here that J.E.B. Stuart’s supply train was attacked by Federal cavalry and artillery. Soldiers from both sides of the Upperville skirmish went on to the fateful fight at Gettysburg just days later.

Built about 1802, Goose Creek Stone Bridge is now on the National Register of Historic Places. It is the largest stone turnpike bridge in Northern Virginia and a popular stop for portraits and pictures.

The Mosby Cluster of Wineries

Heading east on Mosby Highway (US-50) from Goose Creek, you’ll have your choice of tastings at a number of up-and-coming wineries. The first one you’ll encounter is Boxwood Estate Winery (2042 Burrland Road, a quick jog to the right on The Plains Road from Middleburg). Then comes Greenhill (23595 Winery Lane), Cana Vineyards and Winery (38600 John S. Mosby Highway), Chrysalis Vineyards (39025 John Mosby Highway), and finally, after a northward swing up US-15, Quattro Goomba’s Winery (22860 Monroe-Madison Memorial Highway).

The Mosby Cluster wineries boast stunning views, top-notch tastings, and understated reds reminiscent of those from Burgundy and Bordeaux. Goomba’s is a great stopping point for a little nosh at the end of an afternoon of wine tasting. The winery is paired with a pizza shop that dishes up square-cut Sicilian-style pizza. You’ll have to watch the time, though—at Goomba’s, the last tastings and eat-in pizza orders are taken at 5:30 p.m.

Buckland Farm Market

4484 Lee Highway, Warrenton

To return to Warrenton, head south on Route 15, then turn right on Route 29 south. You’ll know you’ve hit the Fauquier County line when you see regional favorite Buckland Farm Market on your right. Buckland has been in business in one form or another for nearly thirty years. The family-owned and operated market has the feel of a country store with the selection of a larger grocery. In addition to seasonal produce, meats, and baked goods (many made by market co-owner Sherry Lynn Coffey), Buckland offers shelves upon shelves of knick-knacks, soup and baking mixes, local honeys, syrups, and Buckland-brand jams and jellies. TOE Jam, which takes its name from its mix of tangerines, oranges, and elderberries, is a hit with the kids, while the adult set might better appreciate the sweet kick of Moonshine Jelly.  Buckland is open from 9 a.m. – 7 p.m. Monday through Saturday and 9 a.m. – 6 p.m. on Sunday throughout the spring and summer. Hours change during its fall festival, and Buckland moves to a shorter winter schedule after New Year’s. More information, including a list of what’s in season at the market, is available at



National Kids to Parks Day takes place at Sky Meadows from 11 a.m – 3 p.m. on Saturday, May 20th. Visit the park for geocaching adventures, Junior Ranger activities, Family Discovery Backpacks, and a chance to check out the park’s Explorer Outpost and new outdoor classroom and family trail, the Children’s Discovery area.

The 58th annual Hunt Country Stable Tour will take place Memorial Day weekend, May 27th and 28th. Area farms and equestrian facilities, including Banbury Cross Polo, the circa-1797 Rock Hill Farm, and Virginia Tech’s exceptional MARE Center, will be open for tours. Tickets are available at

The Delaplane Strawberry Festival at Sky Meadows State Park also takes place on Memorial Day weekend, May 27th and 28th. Hosted by Emmanuel Episcopal Church with proceeds benefitting the church’s outreach ministries, the festival boasts a petting zoo, hayrides, games, stories, crafts, music, and tours of the historic Mount Bleak House. Festival fare and baked goods will be available for sale, and, of course, strawberries! The strawberry sundaes are a favorite every year, and fresh strawberries are sold on a first-come-first-serve basis—sometimes they are sold out by midday on Sunday, so plan accordingly. Admission is $25 per car ($20 with advance purchase), cash only.


Virginia Tech’s 420-acre MARE Center will be hosting a farm tour of conservation practices on June 3rd with lunch and transportation provided. You can view and register for the classes and events at

The Upperville Colt and Horse Show will take place from Monday, June 5th through Sunday, June 11th. After Monday, when there is no entry fee, admission is $10 per person per day. Reserved box seating and other additional amenities are available at Don’t miss the Terrier Races, a crowd favorite, at 1 p.m. on the 11th.

Katie Fuster
About Katie Fuster 12 Articles
Katie Fuster lives in Warrenton with her husband, children, and rescue animals. For more on this story, drop by her writers’ page at

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