15+ Places to Shop on the Chesapeake Bay Wine Trail

Holidays… after-Christmas sales… birthdays… anniversaries… shopping is a year-round activity, and much more enjoyable with a glass (or bottle, we don’t judge!) of wine in your hand. Below we share a few places to shop on the Chesapeake Bay Wine Trail, where you are sure to find the perfect gift for anyone, for any occasion. Then you can just sit back, sip, slurp, and eat. Take in the vineyard views, listen to music, warm yourself by a cozy fire, and enjoy the merriment with fellow wine lovers.

Shopping Events on the Trail

Each year, the Chesapeake Bay Wine Trail hosts five signature events, during which vendors sell wares of all kinds at select, participating wineries. December’s Holiday Sip & Shop is a dedicated shopping opportunity to stock up on holiday gifts.

    • February: Wine & Cherries Weekend
    • April: Spring Oyster Crawl
    • July: Pour Your Heart Out fundraiser
    • November: Fall Oyster Crawl
    • December: Holiday Sip & Shop

Some Trail members also participate in offsite events, where you purchase their wine and branded merchandise.

Winery Gift Shops on the Trail

Shop without ever leaving the winery! Several Trail members have gift shops stocked with unique items for winery lovers and others. A number of Trail members offer gift cards and branded merchandise, so you can proudly showcase support for your favorite wineries. At all Trail locations, you can purchase wine by the bottle or case for a host/ hostess, celebration, or special occasion.

Oyster jewelry at Ingleside Vineyards
Oyster jewelry at Ingleside Vineyards

An entire room plus part of the Tasting Room at Ingleside Vineyards and Winery holds hundreds of items, all of which are for sale–even the lampshades! Find something special for wine lovers and non: housewares and decorative furnishings, artwork and antiques, wine accessories, gourmet foods, seasonal/holiday items and more! Love, love, love Ingleside? Find logo merchandise such wine glasses, mugs, clothing, and hats. Ingleside offers 10% off cases of wine everyday (20% for wine club members) and occasional special sales. Wine gift bags are available, as are electronic and physical gift cards.

General’s Ridge Vineyard’s GRV Cozy Corner Gifts, located in the winery’s Tasting Room, has a variety of interesting, seasonal gifts for him, her… everyone! Find the perfect piece of jewelry, wine tumbler, wine glass marker, GRV t-shirts and sweatshirts or cozy neck warmer. Receive a 10% discount off a 6-bottle purchase and 15% off twelve bottles. Military and industry guests get 10% off all the time. Purchase gift cards online or in-person.

Gifts at General's Ridge Vineyard
Gifts at General’s Ridge Vineyard

Cork art, wine bottle wind chimes, painted wine glasses, and wine accessories are just some of the rotating items you’ll find in the gift shop at Good Luck Cellars (GLC.) Additionally, GLC frequently invites local vendors to the winery during events to sell crafts and handmade goods. Wear your love of GLC proudly, with Good Luck Cellars-branded shirts, sweatshirts, hats, etc. Look for special sales throughout the year (such as Mystery Case sales), as well as discounts up to 15% (20% for wine club members) on bulk bottle purchases.

Rivah Vineyards at the Grove is back in 2024 with a special offer for brides and grooms. Beginning January 16, 2024, Rivah Vineyards will be open Tuesdays from 3 to 7 pm (in addition to regular hours) for couples planning their weddings. Preferred vendors will periodically be onsite allow couples to taste the catering, cakes and desserts, see photography styles, etc. The winery is also hosting vendors for the 2nd Annual Northern Neck Middle Peninsula Wedding Expo Sunday, March 10, 2024, from 1 to 4 pm. Every day, first responders receive a 10% discount, as do those who purchase wine by the case.

Though The Dog and Oyster is closed for the season (vineyard requests can be accommodated by contacting the winery), its sister property Hope & Glory Inn is open daily. In the Gift Shop, located on the perimeter of the boutique hotel’s fine dining restaurant, The Colonnade, find Dog and Oyster-branded t-shirts, hats and sweatshirts. Gift certificates are available or purchase a case of a wine for a 15% discount.

Shopping Spots Along the Chesapeake Bay Wine Trail

Gift items at Ditchley Cider
Gift items at Ditchley Cider

The Chesapeake Bay Wine Trail stretches the length of the Northern Neck of Virginia (with one member across the Rappahannock River on the Middle Peninsula.) Along the 65-mile Trail are unique small towns with fun shops and boutiques, art galleries, antiques stores, and other retail opportunities. Make it a shopping weekend (or longer!) by planning a stay in this beautiful scenic and historic region.

Upper Northern Neck

Located at the gateway of the Northern Neck (NNK), just 60 miles south of Washington, DC, are Trail wineries Ingleside Vineyards and Monroe Bay Winery. This section of the NNK is home to historical sites such as George Washington’s Birthplace National Monument and Stratford Hall. Both attractions have gift shops chock-full of toys, home decor, local foods, books, educational products and more to enhance your visit.

Middle Peninsula & Northern Neck

Caret Cellars is located near Tappahannock on the Middle Peninsula. Across the Rappahannock River, on the Northern Neck, find fellow Trail members General’s Ridge Vineyard and Rivah Vineyards at the Grove. In this region, you’ll find antiques stores, gift shops, and specialty clothing boutiques. Visit the Westmoreland Museum Shop for souvenirs and gifts such as jewelry, stationary, art, handbags, foodstuff, rare books, apparel, home furnishings and so much more!

Lower Northern Neck

Cutting boards at Good Luck Cellars
Cutting boards at Good Luck Cellars

Four members of the Chesapeake Bay Wine Trail are located on the southern tip of the NNK: The Dog and Oyster, Good Luck Cellars, and Jacey Vineyards. Also located in this area is Ditchley Cider Works & Farm, whose Tasting Room is closed for the season, but open for online pickup orders of ciders, meats, poultry, lard, and eggs.

The commercial hub of this region is the Town of Kilmarnock, where Trail members Ditchley Cider Works and Good Luck Cellars are located. Renowned for its award-winning, pedestrian-friendly Main Street, Kilmarnock is home to more than fifty-five locally-owned, premier retailers. Along the main drag and bustling side streets, visitors find charming shops offering men’s and women’s apparel, antiques and estate pieces, pet supplies, outdoor and recreational gear (including crab and oyster pots, as well as marine, fishing and boating supplies), gift items and household needs. During special events in Kilmarnock Town Centre Park, visitors will find artisans and vendors selling handcrafted items and other specialty goods. The Town boasts over 500 businesses, including big box retailers on the northern end of its main street.

Town of Kilmarnock, VA
Town of Kilmarnock, VA

On the southern tip of the Northern Neck is the Town of Irvington, a coastal village along the Rappahannock River. Find specially-curated apparel, accessories and gifts; art galleries; jewelry stores; needlepoint and quilting supplies; community bookshop; gourmet foods and beverages; self-care essentials; and, of course, Trail winery The Dog and Oyster.

Whatever you are shopping for–and for whomever you are shopping for, you are sure to find it on the Chesapeake Bay Wine Trail. Extend your visit! Check out our Itineraries page to find places to stay, eat, and explore. Visit our Wineries page to view current operating hours of Trail members.

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