Listing is for planning only. We do not endorse any specific winery and some may be outside our service area.
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Tip: Most groups visit 3-4 stops in a day.
39060 Little River Tpke., Middleburg, VA 20117
🍷 Perched on a Middleburg bluff with Bull Run mountain views for miles, 50 West Vineyards pours 100% Virginia wine that tastes as good as the scenery looks.
38593 Daymont Ln., Waterford, VA 20197
🍷 Sip handcrafted wines and brews at this working farm winery in Waterford, where vineyard views, a dog park, and easygoing countryside charm make for a perfect roaming stop.
14001 Harpers Ferry Rd., Hillsboro, VA 20132
🍇 Sip your way through the seasons at 868 Estate Vineyards in Hillsboro, where wine, music, and art come together against gorgeous Loudoun countryside views.
16413 James Monroe Hwy., Leesburg, VA 20176
🐸 Sip your way through Loudoun County at this veteran and woman-owned Leesburg vineyard, where good wine, live tunes, and a dog-friendly patio make for easy afternoons.
40614 Charles Town Pike, Paeonian Springs, VA 20129
🍏 Sip small-batch cider and wine grown right on Long Stone Farm, where heirloom apples and Civil War-era barns share the view of Short Hill Mountain.
18755 Foggy Bottom Rd., Bluemont, VA 20135
🍷 Perched 951 feet up on the Blue Ridge, Bluemont Vineyard pours award-winning Virginia wines with a side of jaw-dropping Loudoun Valley views over the family farm below.
2042 Burrland Ln., Middleburg, VA 20117
🍷 Sip Bordeaux-style blends at Boxwood Estate, a former NFL owner's passion project tucked into the Middleburg countryside—swirl, sip, repeat.
35226 Charles Town Pike, Purcellville, VA 20132
🍇 Sip family-made wines with Blue Ridge views at this Purcellville vineyard, where a pizza oven and pavilion make lingering over a glass feel like the whole point.
36888 Breaux Vineyards Ln., Purcellville, VA 20132
🍇 Sip your way through 400+ acres of vines climbing Short Hill Mountain, with Blue Ridge views stretching out from the terrace - Loudoun's wine game runs deep here.
38600 Little River Tpke., Middleburg, VA 20117
🍷 Roll into Middleburg's horse-and-wine country for a glass at Cana Vineyards, where rolling Loudoun vistas make the perfect backdrop for a lazy sip-and-stroll afternoon.
40817 Browns Ln., Waterford, VA 20197
🍷 Tucked in the barn on Browns Lane, Carriage House Wineworks pours award-winning Petit Verdot and Tannat that keep stealing medals from Governor's Cup judges—sip and see what the fuss is about.
17956 Canby Rd., Leesburg, VA 20175
🍷 Casanel Vineyards trades DC bustle for Loudoun calm, pouring family-made Virginia wines from hand-harvested grapes just an hour from the city.
39025 Little River Tpke., Middleburg, VA 20117
🍇 Sip Norton wines grown right on Virginia soil at Chrysalis Vineyards, then pair a glass with wood-fired pizza and farmstead cheeses out on the farm.
14635 Corkys Farm Ln., Waterford, VA 20197
🍎 Sip small-batch ciders and specialty wines at this family-run Loudoun County gem, where picnics, pups, and kids are all welcome on the pretty Waterford grounds.
41255 Annas Ln., Lovettsville, VA 20180
🍷 Sip your way through Lovettsville at Creek's Edge, where timber beams, a stone fireplace and vineyard views make lingering over a flight feel like the only plan worth having.
13235 Milltown Rd., Lovettsville, VA 20180
🍇 Tucked between the Short Hill and Furnace Mountains, Domaine Fortier pours small-lot, hand-crafted wines born from carefully chosen Catoctin Valley terroir - sip slow and soak in the view.
14727 Mountain Rd., Hillsboro, VA 20132
🍷 Sip your way through four decades of family-crafted Virginia wine at this 318-acre Short Hill Mountain estate, where vineyard views and old-world Greek charm meet new-world flavor.
15100 Harrison Hill Ln., Leesburg, VA 20176
🍷 Sip estate-grown wines vinified right on-site at Eagletree, then let the kitchen's seasonal menu and craft beer or cocktail specials round out the visit in Leesburg's rolling countryside.
19600 Lincoln Rd., Purcellville, VA 20132
🍷 Roll up to Endhardt Vineyards in Purcellville and let someone else handle the driving while you handle the tasting — Loudoun's rolling wine country never looked so easy.
15669 Limestone School Rd., Leesburg, VA 20176
🍇 Fabbioli Cellars keeps it real out in Loudoun's countryside — earth-friendly, award-winning wines poured by folks who actually make the stuff, no pretense included.
40325 Charles Town Pike, Hamilton, VA 20158
🍷 A family-run boutique winery in Loudoun's wine country where you can sip a flight on the deck, share a bottle in the backyard, or picnic with views of the neighboring horse farm.
23075 Evergreen Mills Rd., Leesburg, VA 20175
🍇 Pass through the stone archway into Fleetwood's garden oasis, where lush vines, sophisticated pours, and pastoral Loudoun views make for a seriously relaxing pit stop on your tour.
35113 Snickersville Tpke., Round Hill, VA 20141
🍇 A family-run winery on 42 bucolic acres in Round Hill, where "Good Spirit" (their family name, translated) says it all - sip Virginia-grown wine among gardens built for slowing down.
23595 Winery Ln., Middleburg, VA 20117
🍷 Sip award-winning, 100% Virginia-grown wines paired with a mezze menu at Greenhill Vineyards, Loudoun's boutique gem tucked into breathtaking hunt country. Adults-only, all charm.
43301 Spinks Ferry Rd., Leesburg, VA 20176
🍷 Tucked off Spinks Ferry Rd in Loudoun's wine country, Hidden Brook Winery is the perfect excuse to let someone else drive while you swirl, sip, and savor.
12202 Axline Rd., Lovettsville, VA 20180
🍷 Tucked off the beaten path in Lovettsville, Hiddencroft grows nearly every grape it pours, then pours it inside a restored farmhouse with vineyard views. Sip on the deck, linger by the fire pit, let the estate-grown wine do the talking.
36716 Charles Town Pike, Hillsboro, VA 20132
🍷 Sip your way through Loudoun's countryside at Hillsborough Winery, Brewery & Vineyard, where wine and beer share the same roof (and your bus can handle the designated driving).
36140 Charles Town Pike, Purcellville, VA 20132
🍇 Sip something local at Kalero Vineyard, where Blue Ridge views meet a historic 1834 barn nicknamed Heartstone for the heart-shaped stone found on the farm.
317 Hooffs Run Dr., Alexandria, VA 22314
🍏 Sugar-free, unpasteurized, and unfiltered, Lost Boy Cider proves apples can be an adventure — sip real-ingredient brews with hops, cranberry, or pineapple in their Alexandria taproom.
495 E. Washington St., Middleburg, VA 20117
🍏 Sip your way through Mt. Defiance's handmade ciders and spirits, crafted in small batches at their Middleburg barn since 2014 - award-winning, homegrown, and dangerously easy to love.
13274 Sagle Rd., Hillsboro, VA 20132
🎶 Beer, wine, cider, and seltzer all crafted on one Hillsboro farm, best sipped with a side of live music and gorgeous countryside views.
7 Loudoun St. SW, Leesburg, VA 20175
🍷 Sip estate-grown Loudoun County wines at this downtown Leesburg tasting shop, born from a 30-acre Bluemont vineyard where elevation and soil do the heavy lifting.
23583 Fleetwood Rd., Aldie, VA 20105
🍷 Sip your way through 35 acres of preserved Loudoun farmland at this old-school 18th-century farmhouse turned winery, complete with a barn, outdoor bar, and plenty of room to spread out.
18050 Tranquility Rd., Purcellville, VA 20132
🍷 Sip Grüner Veltliner or Blaufränkisch grown right on Tranquility Farm's Purcellville hillside, where the tasting room sits literally above the vines that made your glass.
1500 Crenshaw Rd., Upperville, VA 20184
🍇 Sip Virginia-grown wines with sweeping Hunt Country views at this 300-year-old family farm turned vineyard, where charcuterie and easy flights make for a laid-back, no-rush kind of afternoon.
19925 Hogback Mountain Rd., Leesburg, VA 20175
🍇 Perched atop 300 mountain acres in Leesburg, Stone Tower Winery pairs sweeping Loudoun views with pours worth savoring - bring friends, leave the driving to us.
36580 Shoemaker School Rd., Purcellville, VA 20132
🍯 Sip your way through Loudoun's wine country with a twist at Stonehouse Meadery, where honey wine takes center stage instead of grapes. A sweet little detour worth buzzing about.
38295 Fremont Overlook Ln., Purcellville, VA 20132
🍷 Sip award-winning, 100% Virginia-grown wine at a restored Amish barn in the Loudoun foothills, where mountain views and golden sunsets steal the show.
39892 Old Wheatland Rd., Waterford, VA 20197
🍷 Sip mischievously good 100% Virginia-grown wine in a barn built by the Amish, where 25 acres of Catoctin views make Waterford's rascally hideout worth the detour.
16804 Hamilton Station Rd., Hamilton, VA 20158
🐄 Sip estate-grown wine inside a century-old dairy barn turned rustic-chic tasting room, where Loudoun's rolling vineyard views come standard with every glass.
32 S. King St., Leesburg, VA 20175
🍷 Sip your way through Lost Creek's Loudoun County pours without leaving downtown Leesburg, right on S. King St. A cozy little detour for wine lovers who'd rather taste than trek out to the vines.
38516 Charles Town Pike, Waterford, VA 20197
🍷 Sip award-winning Virginia wines with sweeping Blue Ridge and Catoctin Valley views at this boutique Waterford gem, where the vibe stays relaxed and the pours stay thoughtful.
18548 Harmony Church Rd., Hamilton, VA 20158
🍷 Sip European-style Virginia wines in a century-old bank barn or creekside under shady old trees—28 acres of former farmland turned Loudoun vineyard bliss.
12944 Harpers Ferry Rd., Purcellville, VA 20132
🍇 Family-run and vineyard-view-rich, Two Twisted Posts pours Virginia wine and beer with live music often filling the patio air in Purcellville's rolling countryside.
40405 Browns Ln., Waterford, VA 20197
🍷 Tucked into the Blue Ridge countryside near Waterford, this farm winery pours its own vintages alongside honey, apples, and other homegrown goodies straight from the land it's rooted in.
16031 Hillsboro Rd., Purcellville, VA 20132
🍷 Sip your way through Loudoun County at Walsh Family Wine, where the pours are a genuine taste of the local vineyards and the tasting room vibes have earned some serious local bragging rights.
106A South St. SE, Leesburg, VA 20175
🍎 Wild Hare Cider Cabin pours craft hard ciders pressed from Shenandoah Valley apples, a cozy Leesburg pit stop for your crew to sip local and unwind between limo laps.
35521 Sexton Farm Ln., Round Hill, VA 20141
🍷 Tucked into the rolling farmland of Round Hill, Williams Gap Vineyard is the kind of spot where a glass of Loudoun-grown wine and a good view just make sense together.
38906 Mt. Gilead Rd., Leesburg, VA 20175
🍷 Perched atop Catoctin Ridge, Loudoun County's original winery pours award-winning bottles with panoramic views of the valley and Blue Ridge Mountains as your backdrop - sip accordingly.
19381 Dunlop Mill Rd., Leesburg, VA 20175
🍇 Sip estate-grown reds, whites, and a proudly "intentional" rosé at this family-run Loudoun farm, where sheep, cattle, and 19 blocks of vines have shared the land since 1949.
1808 Leeds Manor Rd., Delaplane, VA 20144
🍇 Sip clean, native-yeast Virginia wine beneath the Blue Ridge canopy at Arterra, then wander their forest sculpture trail for a little wine-and-wonder combo.
11083 John Marshall Hwy., Delaplane, VA 20144
🍷 Roll onto the Delaplane wine trail for Aspen Dale's barn-set sips and rolling Piedmont views, with kids and pups happily along for the ride.
3623 Grove Ln., Delaplane, VA 20144
🍷 Sip award-winning wines and small-batch brews at Barrel Oak, where Blue Ridge views roll out beneath you in Delaplane's Piedmont countryside—easy to see why it's a Fauquier favorite.
5535 Blue Valley Way, Delaplane, VA 20144
🍷 Sip award-winning Virginia wines while the Blue Ridge Mountains show off in the background at this family-run Delaplane vineyard - bring your camera, leave the rush at home.
13400 Crimson Ln., Linden, VA 22642
🍷 Perched on the slopes of Blue Mountain in Linden, Capstone Vineyards pairs sweeping views with small-batch, family-crafted wines grown from the mountain's own unique soil.
3238 Rail Stop Rd., Markham, VA 22643
🍷 Tucked into the Blue Ridge Mountains, this family-run winery lets you sip Tannat and other bold reds while owner Howard O'Brien himself might be pouring behind the bar.
4615 Remount Rd., Front Royal, VA 22630
🍷 Sip small-batch reds and whites at this Front Royal estate winery, where the tasting room view stretches clear across the valley to the mountains beyond.
5909 Long Fall Ln., Delaplane, VA 20144
🍏 Sip small-batch cider by the fire pit, dunk your toes in Thumb Run Creek, or let the pup lead you down a wooded trail at this 90-acre Delaplane orchard escape.
13334 Crimson Ln., Linden, VA 22642
🍷 Sip something estate-grown at Crimson Lane Vineyards, a family-owned Linden winery where the Blue Ridge Mountains steal the show right along with the wine.
2187 Winchester Rd., Delaplane, VA 20144
🍾 Sip sparkling rosé with a side of Cobbler Mountain views at this Delaplane favorite, where Wall Street Journal-approved wines meet the kind of hospitality that makes you linger.
3310 Freezeland Rd., Linden, VA 22642
🦊 Perched on Blue Mountain in Linden, Fox Meadow pairs sweeping Blue Ridge views with a cozy tasting room, friendly pours, and a dog-friendly patio for good measure.
8141 Opal Rd., Warrenton, VA 20186
🍇 Sip estate-grown wines at Granite Heights, where the same winemaker has been crafting bottles since 2008 - including Governor's Cup winners like Humility. A quiet corner of Fauquier wine country worth the detour.
3708 Harrels Corner Rd., Linden, VA 22642
🍇 Tucked in the Blue Ridge, Linden Vineyards pours single-vineyard Chardonnay, Sauvignon Blanc, and Bordeaux blends grown just steps from the tasting room, all in the name of good, honest terroir.
8295 Falcon Glen Rd., Warrenton, VA 20186
🍇 Sip your way through Mediterranean-inspired wines at this Warrenton boutique winery, crafting and aging every bottle on-site since 1961 amid rolling Virginia countryside.
10075 Lees Mill Rd., Warrenton, VA 20186
🍷 Molon Lave Vineyards in Warrenton pours gold-medal-winning Virginia wines - Petit Manseng to Cab Sauvignon - amid vineyard views built for easy sipping and live tunes.
11409 Marsh Rd., Bealeton, VA 22712
🍷 Sip your way through generations of Portuguese winemaking tradition at this Bealeton gem, where family legacy fills every glass and the grounds practically beg for a lingering toast.
2747 Leeds Manor Rd., Markham, VA 22643
🍷 A Virginia classic since 1974, Naked Mountain pours crowd-pleasers like Chardonnay/Riesling and Raptor Red across forty-one Blue Ridge acres made for lingering with friends.
6190 Georgetown Rd., Broad Run, VA 20137
🍷 Sip your way through Fauquier County at Pearmund Cellars, a laid-back Broad Run winery where the wine's the star and you just bring the good company.
4366 Stillhouse Rd., Hume, VA 22639
🍷 Sip your way through centuries of Virginia wine history at Philip Carter Winery, tucked into the rolling hills of Hume—vineyards, tastings, and a whole lot of charm await.
2550 Delaplane Grade Rd., Delaplane, VA 20144
🍇 Roll up to RdV Vineyards in Delaplane and sip world-class Bordeaux-style blends amid rolling Fauquier hillsides, no designated driver required since your bus already has one.
10100 Three Fox Ln., Delaplane, VA 20144
🦊 Sip your way through Delaplane at Three Fox, where vineyard views meet farm-brewed beer under one roof, because why choose just one buzz when you can double up.
7150 Lineweaver Rd., Warrenton, VA 20187
🍷 Sip small-batch Virginia wine inside a historic barn at Vint Hill Farm Station, where WWII code-breakers once cracked German ciphers - swirl, sip, and soak up some spy history.
92 Schoolhouse Rd., Washington, VA 22747
🍇 Sip something award-worthy on a sun-splashed deck with Blue Ridge views, then curl up in the modern Tuscan tasting room at Gadino Cellars in Rappahannock's wine country.
14706 Lee Hwy., Amissville, VA 20106
🍇 One of Virginia's oldest, most decorated wineries, where hand-picked grapes and oak-aged reds meet genuine family warmth in Rappahannock County.
72 Christmas Tree Ln., Washington, VA 22747
🍷 Sip “George,” Virginia’s #1 red, at this Blue Ridge farm perched near Shenandoah’s Thornton Gap—two tasting rooms, one seriously scenic pour.
200 Viewtown Rd., Amissville, VA 20106
🍇 Sip local pours at this cozy Mom-&-Pop vineyard in Rappahannock County, where friendly winery dogs may wander over to say hello mid-tasting.
43 Narmada Ln., Amissville, VA 20106
🍷 Sip Governor's Cup gold medal winners with a side of India in scenic Rappahannock County, where Virginia terroir meets a genuinely unique twist. A short detour from Shenandoah National Park and Luray Caverns, worth the sip.
162 Gid Brown Hollow Rd., Washington, VA 22747
🍷 Sip small-batch Bordeaux-style pours amid Blue Ridge foothill views at this Rappahannock gem, where award-winning Cabernets and Chardonnays come with a side of medal-winning bragging rights.
14437 Hume Rd., Huntly, VA 22640
🍇 Sip solar-powered, family-crafted wines against the Blue Ridge backdrop at this woman-led Huntly winery, where a grape-growing legacy dating back to 1571 meets seriously good tasting room hospitality.
5 Sharp Rock Rd., Sperryville, VA 22740
🍷 Tucked beneath Old Rag Mountain along the Hughes River, Sharp Rock Vineyards pours award-winning, hand-bottled wines in a 100-year-old barn while you soak up some of Virginia's prettiest scenery.
14325 Trotters Ridge Place, Nokesville, VA 20181
🍷 Sip your way through Effingham Manor's estate-grown wines and beer on a historic Nokesville property built for lingering with friends over a glass or three.
12593 Foremost Ct., Nokesville, VA 20181
🍷 Sip your way through Nokesville Winery's soil-to-bottle lineup, where the flagship Norton grape shares the stage with Sangiovese, Tannat, and a whole porch's worth of easy-drinking blends.
22860 James Monroe Hwy., Aldie, VA 20105
🍕 Wine, beer, and legendary Sicilian pizza collide in a converted horse barn out in the Loudoun countryside - grab a pint, split a pie, and soak up the rustic charm.
15950 Lee Hwy., Centreville, VA 20120
🍷 Sip award-winning Virginia wine on a farm steeped in history, just a stone's throw from D.C. — grab a spot on the lawn or patio and let the countryside do its thing.
4970 Antioch Rd., Haymarket, VA 20169
🍷 Sip award-winning Virginia wines at The Winery at La Grange, a Haymarket estate where every glass comes with a story worth toasting to.
15850 Sunshine Ridge Ln., Gainesville, VA 20155
🍷 Sip something crisp with sweeping country views at this family-owned Gainesville winery, where wine, beer, cider and seltzer all share the menu—grab lawn seating and let the afternoon wander.
13219 Yates Ford Rd., Clifton, VA 20124
🍷 Fairfax County's very first winery, Paradise Springs is a family-run slice of Clifton history where the Kincheloe-Wiles clan pours wines that now stretch coast to coast.
10753 Mountain Run Lake Rd., Culpeper, VA 22701
🌾 Sip award-winning wines, beers, and ciders inside a converted 1950s corn crib on a 130-year-old Culpeper farm, then wander over to the shady black walnut tree with the pups and kids in tow.
18351 Corkys Ln., Culpeper, VA 22701
🍷 Wine, spirits, and beer under one roof at this Culpeper farmhouse-turned-trifecta, with a WWII museum and lakeside views thrown in for good measure.
13270 Alanthus Rd., Brandy Station, VA 22714
🍻 Sip craft beer and cider on a family-owned farm outside Brandy Station, with kids playing nearby and the Blue Ridge Mountains putting on a sunset show.
14674 Rogers Ford Rd., Sumerduck, VA 22742
🍇 Trade the highway hustle for farm quiet at this family-owned Fauquier County winery, where small-batch wines, beers, and ciders come with friendly faces and zero pretense.
6818 River Rd., Fredericksburg, VA 22407
🍇 Sip bold Virginia blends among the vines at Eden Try, where a restored white barn and Manor House set a swoon-worthy scene even if you're just there for the wine.
5621 Courthouse Rd., Spotsylvania, VA 22551
🍷 Sip barrel-aged Cabernet Franc and buttery Chardonnay just miles from Virginia's second-largest lake, where the vibe is pure relaxed lake life - let the bus handle the driving back.
7530 Morris Rd., Spotsylvania Courthouse, VA 22551
🍷 Sip award-winning specialty fruit wines at this family-run Spotsylvania winery, born from the Evans family's love of fishing the four rivers that shape their land.
275 Decatur Rd., Stafford, VA 22554
🍷 Trade the highway for Tuscany at Potomac Point, where Stafford's rolling vines pour out award-winning wines and a full bistro menu to match, no passport required.
11109 Plank Rd., Spotsylvania, VA 22553
🍇 Sip Cabernet under shady trees at this historic Spotsylvania farm vineyard, then wander over to sister spot 1781 Brewing Co. for a fresh pour and some sunset tunes.
75 S. 3rd St., Warrenton, VA 20186
🍏 Hop off in Warrenton and let the Wild Hare pour you something crisp - craft hard ciders made from Shenandoah Valley apples, no orchard trek required.
Let us handle the driving so your group can enjoy every sip. Luxury limos, SUVs, and party buses available for groups of 2 to 40+. 🍷✨
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