Most 'dog-friendly' lists round up anywhere a dog is legally allowed on a patio. This trail is stricter: every one of the six stops welcomes leashed dogs inside the tasting room itself, which is what actually matters on a hot afternoon or a cold one. Start at Willowcroft on Catoctin Ridge — Loudoun's oldest winery (1984), where dogs are welcome inside a rustic 1870s barn and picnics are encouraged. Drop down to Stone Tower's all-ages Harvest Barn near Leesburg (the 21+ Tower View room next door is the one exception on the trail), then up to Hidden Brook's hand-built Lucketts log cabin, where dog treats and water bowls are kept on hand. The trail's two highlights for off-leash running are next: 8 Chains North in Waterford has a dedicated dog park beside the vines, and Bluemont Vineyard's 951 tasting room keeps a fenced off-leash dog run alongside its indoor welcome. Finish in Middleburg at Cana, where the family- and dog-friendly ground floor (the upstairs is 21+ adults-only) hands out treats and bowls alongside Governor's Cup reds. Leash up between stops and you have a genuine dog-and-wine day.
At a glance
- Every stop on this trail welcomes leashed dogs inside the tasting room itself — not just on the patio.
- Two of the six (8 Chains North and Bluemont Vineyard) have dedicated off-leash dog parks or runs.
- The trail spans Leesburg and the Lucketts corridor, Waterford, Bluemont, and Middleburg, so it works as a full dog-and-wine day.
Getting around: Keep dogs leashed everywhere except the two off-leash runs at 8 Chains North and Bluemont Vineyard. A few stops restrict dogs from upstairs or adults-only areas — check the venue page before you go.
The stops
Open route in Google Maps (opens in new tab)
Map view
- Winery
Each dot is a stop on this trail. Tap a dot to open the venue.
- WineryPrint details: 38906 Mt. Gilead Rd, Leesburg, VA 20175 (703) 777-8161 Mon 12:00-17:00; Fri 12:00-19:00; Sat 12:00-19:00; Sun 12:00-17:00
- WineryPrint details: 19925 Hogback Mountain Road, Leesburg, VA 20175 (703) 777-2797 Closed Tue–Wed (typical)
- WineryPrint details: 43301 Spinks Ferry Rd, Leesburg, VA 20176 (703) 737-3935 Sat 11:30-18:00; Sun 12:00-17:00
- Winery
- Winery
- 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)
Explore the regions on this trail
A matching day plan
Trail field sheet
Dog Day Out Trail
Six stops where leashed dogs are welcome inside — including two with dedicated off-leash dog parks.
Map view
- Winery
Stops are positioned relative to downtown Leesburg.
- 1
Willowcroft Farm Vineyards
Address: 38906 Mt. Gilead Rd, Leesburg, VA 20175
Phone: (703) 777-8161
Hours: Mon 12:00-17:00; Fri 12:00-19:00; Sat 12:00-19:00; Sun 12:00-17:00; Open Fri-Sat noon-7pm and Sun-Mon noon-5pm; last call 30 minutes before close.
Fees: Flights run $20-$40, depending on the tasting format.
Reservations: Walk-ins welcome
Dogs: Welcome inside and out Family: All ages welcome
Facts checked 2026-07-07
- 2
Stone Tower Winery
Address: 19925 Hogback Mountain Road, Leesburg, VA 20175
Phone: (703) 777-2797
Hours: Closed Tue–Wed (typical); Open Thu-Mon 11am-6pm; final pour at 5:30pm; closed Tue-Wed. Verify around holidays and estate events.
Fees: Harvest Barn tasting about $25; Cellar Tour $45, Signature Experience $100, and Estate Experience up to $175.
Reservations: Walk-ins welcome
Dogs: Welcome inside and out Family: All ages welcome
Facts checked 2026-07-07
- 3
Hidden Brook Winery
Address: 43301 Spinks Ferry Rd, Leesburg, VA 20176
Phone: (703) 737-3935
Hours: Sat 11:30-18:00; Sun 12:00-17:00; Per the official site (2026): Saturday 11:30am-6pm and Sunday 12-5pm; closed Monday-Friday. The kitchen closes one hour before last call, and the winery occasionally closes early for private…
Fees: Flights are $17 for any four wines (3 oz pours, seasonal beverages available on request); a guided table-side tasting of all nine wines is $20. (Older third-party listings still cite…
Reservations: Walk-ins welcome
Dogs: Welcome inside and out Family: All ages welcome
Facts checked 2026-07-07
- 4
8 Chains North Winery
Address: 38593 Daymont Ln, Waterford, VA 20197
Phone: (571) 439-2255
Hours: Open daily (typical); Open daily: weekdays roughly noon-6pm, with later evenings Wednesday (to about 8:30pm for trivia) and Friday (to about 9pm); weekends 11am-6pm — verify seasonally.
Fees: Walk-in tastings run about $18 for six wines; self-guided four-pour flights about $20; elevated tour-and-barrel-tasting experiences about $45 with a chocolate-pairing add-on around $8 (verify seasonally).
Reservations: Walk-ins welcome
Dogs: Welcome inside and out Family: All ages welcome
Facts checked 2026-07-07
- 5
Bluemont Vineyard
Address: 18755 Foggy Bottom Rd, Bluemont, VA 20135
Phone: (540) 554-8439
Hours: Open daily (typical); Open daily: Mon-Fri 11am-5pm, Sat 11am-7pm, Sun 11am-5pm; verify seasonally and around special events.
Fees: Standard tasting ~$15, Reserve ~$25; Elevated and Food & Wine pairing experiences ~$35-$45
Reservations: Reservations recommended
Dogs: Welcome inside and out Family: All ages welcome
Facts checked 2026-07-07
- 6
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
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.