Hunt country is the through-line here. The stretch of Route 50 from Aldie through Middleburg pairs Loudoun's most polished tasting rooms with its deepest horse-and-hound heritage, and this trail strings six of them into a half-day that mixes serious wine with a walkable town finish. Open at Chrysalis, home of the world's largest Norton planting in the Middleburg AVA, then climb to Greenhill's 1762 stone manor — one of the oldest standing structures on any Virginia winery, set on a working horse farm against a Blue Ridge and Bull Run backdrop (21+ only). Drop west to 50 West's bluff-top panorama, where floor-to-ceiling windows put Bull Run Mountain behind every seat, then loop back to Cana for 2022 Virginia Governor's Cup reds and a dog-and-family-friendly ground floor. Lost Barrel's 70-acre horse farm brewery (next door to Salamander Resort) brings a full kitchen and a family-friendly lawn, and the trail ends on foot in downtown Middleburg at Mt. Defiance, where a rustic barn pours cider and rum a block from the boutiques. Base here if your ideal day mixes tastings with a landmark-inn dinner — Middleburg's restaurant row is the best in the county.
At a glance
- Greenhill's stone manor dates to 1762 — one of the oldest standing structures on any Virginia winery.
- Chrysalis grows the world's largest planting of Norton, Virginia's native grape.
- The trail ends on foot in downtown Middleburg, with Mt. Defiance's cider barn a block from the boutiques.
Getting around: Route 50 is the spine — easy driving, but it's horse country, so watch for equestrian crossings. Base in Middleburg and the whole trail is a 15-minute radius; finish in town for dinner on Middleburg's restaurant row.
The stops
Open route in Google Maps (opens in new tab)
Map view
- Winery
- Brewery
- Cidery
Each dot is a stop on this trail. Tap a dot to open the venue.
- WineryPrint details: 39025 Little River Turnpike, Middleburg, VA 20117 (540) 687-8222 Open daily (typical)
- Winery
- WineryPrint details: 39060 John Mosby Highway (Route 50), Middleburg, VA 20117 (571) 367-4760 Closed Tue–Wed (typical)
- WineryMiddleburg · $$
Cana Vineyards & Winery of Middleburg
Governor's Cup reds with a dog-and-kid-friendly ground floor
Print details: 38600 Little River Turnpike, Middleburg, VA 20117 (703) 348-2458 Closed Tue–Wed (typical) - BreweryPrint details: 36138 Little River Turnpike, Middleburg, VA 20117 (540) 326-4631 Mon 12:00-20:00; Thu 12:00-20:00; Fri 12:00-21:30; Sat 11:00-21:30; Sun 11:00-20:00
- CideryPrint details: 495 E Washington St, Middleburg, VA 20117 (540) 883-3176 Wed 12:00-18:00; Thu 12:00-18:00; Fri 12:00-19:00; Sat 12:00-19:00; Sun 12:00-18:00
Explore the regions on this trail
Trail field sheet
Middleburg Hunt Country Trail
The Route 50 stretch through Middleburg and Aldie — polished tasting rooms, deep horse-and-hound heritage, and a 1762 stone manor.
Map view
- Winery
- Brewery
- Cidery
Stops are positioned relative to downtown Leesburg.
Cell service is patchy in western Loudoun — print or screenshot this.
- 1
Chrysalis Vineyards at The Ag District
Address: 39025 Little River Turnpike, Middleburg, VA 20117
Phone: (540) 687-8222
Hours: Open daily (typical); Open daily from noon; closes early evening, later Fri-Sun, but exact closing times vary by season — verify before visiting.
Fees: Self-guided tastings ~$15
Reservations: Walk-ins welcome
Dogs: Outdoors only Family: All ages welcome
Facts checked 2026-07-07
- 2
Greenhill Vineyards
Address: 23595 Winery Lane, Middleburg, VA 20117
Phone: (540) 687-6968
Hours: Open daily (typical); Open daily noon-6pm; closed Thanksgiving, Christmas Day, and New Year's Day, with holiday/Christmas Eve adjustments — verify before visiting.
Fees: Tasting/flight fees not published online; Loudoun flights typically run ~$15-$25 — confirm current pricing before visiting.
Reservations: Walk-ins welcome
Dogs: Outdoors only Family: Adults 21+ only
Facts checked 2026-07-07
- 3
50 West Vineyards
Address: 39060 John Mosby Highway (Route 50), Middleburg, VA 20117
Phone: (571) 367-4760
Hours: Closed Tue–Wed (typical); Open Thu-Mon; closed Tue-Wed. Later hours Fri-Sat; confirm seasonally.
Fees: Tasting flights are inexpensive (recent reports around $5-$15); private seated tastings are $30/person and must be arranged ahead.
Reservations: Reservations recommended
Dogs: Outdoors only Family: Adults 21+ only
Facts checked 2026-07-07
- 4
Cana Vineyards & Winery of Middleburg
Address: 38600 Little River Turnpike, Middleburg, VA 20117
Phone: (703) 348-2458
Hours: Closed Tue–Wed (typical); Open Mon, Thu, Fri, and Sun noon-6pm; Sat 11am-6pm; last call 5:30pm; closed Tue-Wed. Verify seasonally.
Fees: Self-guided flights are $12 for three wines; guided tastings should be reserved ahead.
Reservations: Walk-ins welcome
Dogs: Welcome inside and out Family: Limited; ask ahead
Facts checked 2026-07-07
- 5
Lost Barrel Brewing
Address: 36138 Little River Turnpike, Middleburg, VA 20117
Phone: (540) 326-4631
Hours: Mon 12:00-20:00; Thu 12:00-20:00; Fri 12:00-21:30; Sat 11:00-21:30; Sun 11:00-20:00; Open Mon noon-8pm, Thu noon-8pm, Fri noon-9:30pm, Sat 11am-9:30pm, Sun 11am-8pm; closed Tue-Wed.
Fees: Brewers Experience Tour with seated six-beer tasting is $25/person; Brewhouse Tour is $10/person with a 12 oz pour; regular flights/pints are a la carte.
Reservations: Walk-ins welcome
Dogs: Outdoors only Family: All ages welcome
Facts checked 2026-07-07
- 6
Mt. Defiance Cider & Distillery
Address: 495 E Washington St, Middleburg, VA 20117
Phone: (540) 883-3176
Hours: Wed 12:00-18:00; Thu 12:00-18:00; Fri 12:00-19:00; Sat 12:00-19:00; Sun 12:00-18:00; Open Wed–Sun afternoons into early evening at The Barn (495 E. Washington St, now the single location, with the upstairs spirits tasting room); Monday is bottle sales only…
Fees: Flights of ciders and small-batch spirits plus glasses, bottles, and cocktails; Thursday patio bar runs $7 cocktail specials. No published flat tasting fee.
Reservations: Walk-ins welcome
Dogs: Welcome inside and out Family: All ages welcome
Facts checked 2026-07-07
Verify before you go: Hours, fees, reservations, and dog/family policies can change. Confirm the details that matter directly with each venue.
Plan it, stay safe, go again
Trails are shareable routes — pair this one with a chauffeured tour, a place to stay, or another trail for the rest of the weekend.