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.
15010 Roddy Rd, Thurmont, MD 21788
🍷 Sip hand-crafted wines grown in ancient Appalachian soil, with Blue Ridge foothill views stretching out around this family-run Thurmont vineyard.
9831 Fox Rd, Frederick, MD 21702
🍷 Tucked high in the Catoctin Mountains, Celebration Cellars hand-crafts small-batch wines the old-fashioned way, plus a cozy on-site B&B for those who don't want the visit to end.
15113 Liberty Road, Mt Airy, MD
🍷 Sip award-winning pours at Elk Run Vineyards, where rolling Frederick County hills, a 1756 winemaker's cottage, and deep-rooted schist soils make for seriously good wine and even better views.
7550 Green Valley Rd, Frederick, MD 21701
🍇 Sip local vintages amid 100 acres of horse-farm views at Hidden Hills, where Frederick County's rolling hills meet Maryland-grown wine in one seriously scenic tasting room.
13601 Glissans Mill Road, Mount Airy, MD
🍷 Sip your way through three generations of family winemaking at this Mount Airy vineyard, born from an old dairy farm back in 1972 and still going strong on rolling hills and good soil.
8830 Old Links Bridge Rd, Thurmont, MD 21788
🍇 Sip your way through Links Bridge Vineyards, a working Thurmont farm winery where homegrown grapes turn into wine worth savoring, with art shows and rotating events keeping things interesting.
14001 Liberty Road, Mount Airy, MD
🍷 Sip your way through Loew Vineyards, where Maryland's only Kosher wines and meads are crafted amid family-run vines in Mount Airy - a laid-back pour with genuine local roots.
8333 Myersville Rd, Middletown, MD
🍇 A family-run boutique winery in Middletown pouring award-winning Maryland wines, from apricot-kissed Albariño to peppery Cabernet Franc — sip your way through the estate's own vines.
8546 Pete Wiles Road, Middletown, MD 21769
🍯 Sip your way through mead done right at this woman-owned Middletown meadery, where the world's oldest alcohol gets an internationally-awarded, 21st-century glow-up.
37 North Market Street, Suite 200, Frederick, MD 21701
🍷 Sip your way through three generations of Maryland winemaking at this downtown Frederick tasting lounge, where estate-grown Chardonnay, Albariño, and Bordeaux blends tell the story of local terroir.
10819 Church Hill Road, Myersville, MD 21773
🍷 Sip estate-grown Cabernet Franc, Albariño, or Teroldego at this 16-acre Myersville vineyard, then grab a mallet for a round of croquet among the vines.
11836 Auburn Road, Thurmont, MD 21788
🌾 One farm, three buzzes - wine, spirits, and 11 house-brewed craft beers, all sipped in a renovated barn with patio views over Thurmont's lavender fields.
6219 Harley Rd, Middletown, MD 21769
🍎 Sip barrel-aged craft cider and port-style dessert wine at Maryland's first certified organic farm, where the orchard views come with a side of resident farm animals.
28712 Kemptown Road, Damascus, MD
🍷 Sip award-winning dry wines against a Sugarloaf Mountain backdrop at this family-run farm winery, where rustic charm meets genuine Maryland hospitality, dogs and skeptics both welcome.
16001 W. Willard Rd, Poolesville, MD 20837
🍷 Sip your way through Poolesville with pours like Liberated Embers Sparkling Vidal Blanc and the Rapture Red Blend, poured by a homegrown crew that clearly loves what they do.
15201 Display Ct, Rockville, MD 20850
🍯 Sip your way through Clear Skies Meadery, where honey wine gets a fun, modern twist worth toasting to on your Rockville pit stop.
18125 Comus Rd, Dickerson, MD 20842
🍇 Roll up to Sugarloaf Mountain Vineyard in Dickerson for rolling hills, rows of vines, and a glass of Maryland-made wine that tastes like the view. Bring the crew, leave the driving to us.
16601 West Willard Rd, Poolesville, MD 20837
🍇 Sip wines made right there on the vineyard, then linger over artisanal bites at the Farmhouse Bistro amid Poolesville's rolling countryside charm.
2315 Stewart Ave, Silver Spring, MD 20910
🍷 Sip, swirl, and maybe even make your own bottle at The Urban Winery, Silver Spring's cozy spot for local wines, craft beers, and outdoor sipping among friends.
15700 Darnestown Rd, Darnestown, MD 20874
🍷 Sip estate-grown Maryland wine on a sprawling lawn with Sugarloaf Mountain views stealing the show, adults-only and refreshingly unpretentious.
24 C St, Laurel, MD 20707
🍷 Sip your way through Laurel at America's first African-owned winery, where handcrafted bottles and a warm welcome tell a story worth toasting to.
8606 Cedarville Rd, Brandywine, MD 20613
🍇 Sip local at Gemeny Winery, a family-run vineyard tucked into a 200-acre working farm just outside D.C., where grapevines meet fields of grain and quiet Maryland woods.
4471 Nicole Dr, Suite D, Lanham, MD 20706
🍷 Sip your way through Imperial 94 in Lanham, where culture-inspired wines like their signature Pink Rosé turn any pour into a celebration worth toasting.
15200 Baden Naylor Road, Brandywine, MD
🍇 Sip your way through a family-owned vineyard where 1877 tobacco fields now grow Albariño, Vidal, and Chambourcin - Napa know-how, Maryland soil, and a genuinely good love story behind every bottle.
11589 Edmonston Rd, Beltsville, MD 20705
🍷 Misfit Winery crafts award-winning wines from imported grapes right here in Beltsville, blending a rebellious streak with serious skill—no tasting room, just pure bottled attitude to track down at festivals or local shops.
15800 Croom Road, Brandywine, MD 20613
🍇 Sip estate-grown wines on a porch overlooking rolling vineyard hills at this family-run Brandywine farm, where red barns and grazing animals set a rustic, feel-good scene.
19906 Aquasco Rd, Aquasco, MD 20608
🍷 Sip award-winning, estate-grown wines in a restored tobacco barn turned cozy tasting room, tucked away in the quiet farmland of Aquasco. A little slice of Southern Maryland charm worth the drive.
12600 Croom Rd, Upper Marlboro, MD 20637
🍷 Sip your way through Prince George's County at Two Lions Vineyards, where rolling vines and Legacy Trail views make every pour feel like a little escape from Upper Marlboro life.
15722 Falls Rd, Sparks Glencoe, MD 21152
🍇 Sip small-batch vintages at this family-run winery tucked into Baltimore County's rolling hills, then wander the vineyard rows for a proper countryside breather between bus stops.
12820 Long Green Pike, Hydes, MD 21082
🍇 Sip your way through eight decades of Maryland winemaking at Boordy Vineyards, where rolling Hydes countryside meets glasses of estate-grown reds, whites, and the occasional Albariño surprise.
17912 York Road, Parkton, MD
🍷 Sip local wines on the sprawling grounds of a historic Parkton farm, picnic in tow and views for miles - Bull House Winery keeps it easy, breezy, and beautifully Maryland.
5300 Hydes Road, Hydes, MD 21083
🍷 Sip your way through Baltimore County at DeJon Vineyard, a Hydes gem known for easygoing wines, live music, and vine-covered views made for lingering.
1700 W 41st St, Baltimore, MD 21211
🍷 Sip small-batch craft wines straight from the source at Baltimore's first urban winery, tucked into a warehouse with tapas and pintxos to match.
14463 Black Ankle Road, Mt Airy, MD 21771
🍷 Sip estate-grown reds and whites at Black Ankle Vineyards, where every bottle comes from grapes grown right on their own Carroll County farms.
400 South Clear Ridge Road, New Windsor, MD
🍏 Roll out to New Windsor for Brothers Ridge Cider, where Maryland-grown apples get turned into handcrafted ciders worth toasting with the whole crew.
1550 Old Westminster Road, Westminster, MD 21157
🍷 Sip site-specific wines and wood-fired farm fare among the rolling hills of Carroll County, where a sibling-run vineyard turns an afternoon into a proper countryside escape.
2962 Nicodemus Road, Westminster, MD 21157
🐍 Sip award-winning wines amid the peaceful vineyard views of Carroll County's hidden gem, a family-owned boutique winery tucked into the Westminster hills.
4236 Main Street, Rohrersville, MD 21779
🍷 Sip award-winning Cabernet Franc and Viognier with Blue Ridge Mountain views as your backdrop at this 100-acre Rohrersville estate—bring the crew, skip the driving.
17039 Castle Hill Road, Hagerstown, MD
🍷 Castle Hill Winery in Hagerstown is the perfect excuse to swap the party bus seats for porch rockers and a glass of something local, even if just for an hour. Bring the crew, leave the driving to us.
19638 Cool Hollow Road, Hagerstown, MD
🍇 Hand-planted, hand-harvested, and steeped in Hagerstown's limestone soil, Cool Ridge Vineyard turns quiet rows of vines into small-batch wines worth the detour.
12840 Red Heifer Winery Lane, Smithsburg, MD 21783
🍷 Sip wine on a hillside that grew peaches, then dairy, then vines - all in the same Naylor family for generations near Smithsburg. Bonus points for guessing how the winery got its name.
14320 Castle Drive, Cascade, MD 21719
🍷 Sip handmade wines inside the former Commanders Castle at Historic Ft. Ritchie, where small-batch pours meet big slices of history in Cascade.
1202 Harmon Rd, Accident, MD 21520
🍏 Sip your way through Accident, Maryland at Branch Bender Cidery, where the cider falls close to the tree and the views are worth the detour.
3320 Swanton Rd, Swanton, MD 21561
🍯 Sip your way through mead and cider at Weber's Crossing in Swanton, where honey wine and Youghiogheny orchard brews share the same cozy roof.
755 Cove Point Rd, Lusby, MD
🍷 Sip your way through Southern Maryland's original winery, where two dozen-plus vines-to-glass creations await your picks in Lusby's laid-back tasting room.
8650 Mackall Road, St. Leonard, MD 20685
🍷 Sip award-winning wines with sweeping views of the Patuxent River at Perigeaux Vineyards, where the vines meet the water and every glass feels like a little victory.
150 Adelina Road, Prince Frederick, MD 20678
🍷 Sip your way through Southern Maryland at Running Hare Vineyard, where tastings, a biergarten, and live music make for a lazy afternoon among the vines.
38713 Golden Beach Rd, Mechanicsville, MD 21666
🍇 Sip your way through Corteau Vineyards, a Southern Maryland haven where vines, sangrias, and easygoing charm come together on the deck - leashed pups and all ages welcome to join the toast.
23190 Newtowne Neck Road, Leonardtown, MD 20650
🍷 Swirl, sip, and repeat at Port of Leonardtown Winery, a laid-back sip of Southern Maryland charm perfect for a group that likes its bus rides followed by a glass (or three).
26781 Laurel Grove Rd, Mechanicsville, MD 20659
🍇 Sip bold, clean wines grown right on this 9-acre family farm in Laurel Grove, where biodynamic roots and Southern Maryland charm fill every glass.
312 Cannon Street, Chestertown, MD 21620
🍷 Sip artisanal wine and vermouth on the farm at Casa Carmen, where pinxtos and tapas pair with easy, unpretentious good company in Chestertown.
12441 Vansant Corner Road, Kennedyville, MD
🐦 Sip award-winning wines grown right on this working Eastern Shore farm, then grab some grass-fed beef while you take in the vineyard views from Kennedyville's coziest tasting room.
22620 Handy Point Rd, Chestertown, MD 21620
🍷 Sip something local on the water's edge at Lands Point, a Chestertown vineyard you can reach by boat, bike, or plain old car - views included, no cork required.
1200 Thompson Creek Rd, Stevensville, MD
🍇 Sip your way through Cascia Vineyards on the Eastern Shore, where Stevensville's countryside charm pairs perfectly with a glass of something local. Let the bus be your designated driver while you toast to the view.
2015 Love Point Road, Stevensville, MD
🍷 Kick back on Kent Island at Chesapeake Manor Vineyard, where award-winning reds and whites are grown right in the Stevensville soil and poured just for your crew.
305 River Shore Ln, Stevensville, MD 21666
🍷 Trade the party bus seat for a vineyard view at Love Point, where Eastern Shore charm meets a glass of something local worth savoring.
8370 Ocean Gateway, Easton, MD 21601
🍷 Swap the party bus seats for winery ones a while and let Far Eastern Shore Winery pour you something local along Easton's Eastern Shore - sipping optional, savoring mandatory.
609 S. Talbot Street, St. Michaels, MD 21663
🍷 Sip your way through St. Michaels at this boutique winery right in town, where handcrafted bottles like the bubbly Gollywobbler blackberry wine wait to be discovered. Grab a glass, linger a while, or stash a few bottles for later exploring.
4225 New Bridge Rd, Vienna, MD 21869
🍷 Sip your way through 14 acres of Eastern Shore vineyard, then let the leashed pup sniff around the picnic area while you relax with a glass in hand.
3155 Noble Farm Rd, Eden, MD 21822
🍷 Sip award-winning wines at Bordeleau, where vineyards meet Wicomico Creek and bald eagles might just crash your picnic on the patio.
3026 Whiteford Rd, Pylesville, MD 21132
🍇 Sip your way through Fiore's Italian-accented wines and spirits, with a vineyard backdrop in Pylesville that's practically begging for a slow afternoon and good company.
1311 W Jarrettsville Rd, Forest Hill, MD 21050
🍷 Roll up to Harford Vineyard & Winery in Forest Hill, a family-owned spot pouring local wine since 2003 - swirl, sip, and let someone else handle the driving.
942 Glebe Rd, Earleville, MD 21919
🍷 Sip something small-batch and farm-fresh at Broken Spoke Winery, where the wines are named after the barnyard crew that inspired them. A laid-back Earleville pour spot made for easy conversation and country charm.
645 Harrington Road, Rising Sun, MD 21911
🍷 Sip your way through Dove Valley Vineyard in Rising Sun, where cotton candy wines and a cozy Cecil County countryside setting make for one delightfully unserious tasting stop.
391 Dodon Rd, Davidsonville, MD 20135
🍷 Sip your way through Davidsonville at this estate vineyard where farming tradition meets serious winemaking science, one unhurried, seated tasting at a time.
3218 Harness Creek Rd, Annapolis, MD 21403
🐸 A historic tobacco barn turned winery minutes from downtown Annapolis — sip estate reds by the fire pits above Harness Creek.
195 Harwood Rd, Harwood, MD 20776
🍷 A family farm winery between Annapolis and the Patuxent — estate-grown Bordeaux-style blends poured in a cozy tasting room.
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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