Chesapeake Bay Wine Trail

Expiration: Jul 1st 2027

The Chesapeake Bay Wine Trail invites you to explore Virginia's coastal wine country one stop at a time. Sign up for the free mobile pass to discover participating wineries and cideries throughout the Northern Neck and Middle Peninsula.

Receive $5 off a tasting during your first check-in at each location, earn chances to win additional prizes throughout the trail, and complete all participating stops for entry into the Grand Prize. One lucky winner and up to five guests will enjoy a private Chesapeake Bay boat cruise featuring light hors d'oeuvres and a curated tasting of wines from participating Trail wineries.

Along the way, enjoy award-winning Virginia Wine, Chesapeake Bay hospitality, and some of Virginia's most scenic coastal landscapes.

Included Venues

See locations on an interactive map.

Ingleside Vineyards

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Producing its first wines in 1980, Ingleside Vineyards is one of the oldest wineries in Virginia. Ingleside produces over 16 varieties of wine from 20 acres of estate-grown grapes. Its wines have won numerous awards and top honors in state, national and international wine competitions. Visitors can enjoy a leisurely afternoon in the European-style courtyard. Frequent winery events, including a summer music series, bring together wine lovers from throughout the region.

What's Included

$5 Off Tasting

Monroe Bay Winery

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Monroe Bay Winery is a waterfront property near the town of Colonial Beach on part of the James Monroe Birthplace Farm land. The Tasting Room is located in a large strawbale barn made of stained glass wine bottle walls. Our location is perfect for events and weddings.

What's Included

$5 Off Tasting

Ditchley Cider Works

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162 acre working farm with over 2000 heritage apple trees and 42 varieties.

What's Included

$5 Off Tasting

Good Luck Cellars

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At Good Luck Cellars, luck is our middle name, and we strive to pour good fortune in each and every glass. We offer estate-grown, hand-crafted wines in Virginia's Historic Northern Neck. Our venue includes a covered, wrap-around porch with fans (or fireplace to knock the chill) that overlook the vineyards and our Grape Vine Patrol Squad (rescue dogs who patrol the vineyards, chasing away wildlife so our grapes have a chance to thrive & later become the wine we all enjoy.).

What's Included

$5 Off Tasting

Jacey Vineyards

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Jacey Vineyards is a charming Virginia winery nestled in the heart of Heathsville, VA. Located at 619 Train Ln, this inviting estate offers a welcoming tasting room, locally crafted wines, and scenic vineyard views. Guests can enjoy relaxed afternoons savoring seasonal varietals, exploring the picturesque countryside, and discovering small-batch wines that reflect the region’s coastal-adjacent terroir. Perfect for a tranquil escape, a weekend outing, or a memorable wine-tue with friends and family.

What's Included

$5 Off Tasting

Rivah Vineyards at The Grove

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Rivah Vineyards at The Grove is a charming Virginia winery perched along the scenic Rappahannock River. Located at 671 Kinsale Bridge Rd, Kinsale, VA 22488, this welcoming hillside estate offers picturesque vineyard views, intimate tastings, and a rotating selection of handcrafted wines. Visitors can enjoy relaxed pours, seasonal events, and a serene backdrop perfect for gatherings, weddings, or a peaceful day by the river.

What's Included

$5 Off Tasting

The Dog and Oyster Micro-Vineyard and Oyster Bar

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The Dog and Oyster Micro-Vineyard and Oyster Bar is a charming waterfront-inspired spot located at 65 Tavern Rd, Irvington, VA 22480. Blending a micro-vineyard ambiance with fresh oysters and seafood, this cozy venue offers a relaxed, maritime-era vibe with seasonal bites, handcrafted drinks, and live-friend vibes. A perfect stop for locals and travelers alike to enjoy small-batch wines, oyster tastings, and a friendly, welcoming atmosphere by the Chesapeake Bay.

What's Included

$5 Off Tasting