Romance on the Chesapeake Bay Wine Trail

You’ve heard it said before: Virginia is for Lovers. What pairs better with love than wine?

Romance abounds here on the Chesapeake Bay Wine Trail. From iconic Virginia love signs (LOVEworks) that provide picture-perfect photo opps, to one of Southern Living’s ‘South’s Best Inns’… from breathtaking nature to cozy corners… love is everywhere on the Trail.

Special “Love” Events

Wine & Cherries Weekend at Ingleside
Wine & Cherries Weekend – Ingleside

Love is the reason–and the season–for many of the events held at participating Trail members’ sites, including five signature Trail events held annually.

Wine & Cherries Weekend is held each February over Presidents Day Weekend. Participating wineries pair their wines with cherry treats, and may also offer live music or other activities.

This year during Wine & Cherries Weekend, Trail winery Monroe Bay Winery is hosting a fundraising benefit concert on Saturday 2/17 to help cover medical and funeral expenses for Alora, a local infant born prematurely who passed away at only 17 days old. Karaoke held at the winery the 2nd & 4th Sundays of the month will help the effort.

The “Pour Your Heart Out” fundraiser is held each July to raise money for charities. Participating Trail wineries donate a portion of sales to a local charity or organization of their choosing.

Oysters at Good Luck Cellars
Oysters at Good Luck Cellars

The Trail’s Spring and Fall Oyster Crawls are held for the love of oysters! Virginia is becoming the “Oyster Capital of the East Coast.” During each crawl, held annually in April and November, participating wineries pair oyster dishes with their wine and may host live music or oyster-related activities.

Individual Trail wineries also hold their own “love” events. For example, each February, Ingleside Vineyards & Winery holds an intimate Valentine’s VIP Tastings event, in which wines not typically found on standard tastings menus are paired with charcuterie. Several wineries offer Valentine’s Day Sip & Paint events, floral design, themed music or other events during the month.

Virginia LOVEworks on the Trail

To date, there are more than 300 LOVEworks around the “Love State”. Posing with Virginia’s love signs and sharing on social media (common hashtags include #LOVEva, #valovesigns, and others) is a popular activity in Virginia. Some travelers even plan roadtrips using Virginia Tourism Corporation’s LOVEwork map as their guide. Here’s where to find LOVEworks on the Chesapeake Bay Wine Trail and surrounding areas.

Ingleside Vineyards

The large-scale LOVEwork featured on the grounds of Ingleside Winery and Vineyards overlooks a scenic wildflower field, complementing the natural beauty and rustic setting of the vineyards. Designed and built by a local craftsman, this love sign is made of large timber frame letters sourced from local Northern Neck white oak, its letters held together by mortise and tenon joinery, a joining method that is thousands of years old and provides a simple design with great strength.

Monroe Bay Winery

Monroe Bay Winery - LOVEwork
LOVEwork at Monroe Bay Winery

When Monroe Bay Winery was building its unique straw bale barn tasting room, it was sure to include plans for a Virginia LOVEworks. Tucked in a romantic and cozy corner of the vast space is LOVE, spelled out with recycled wine bottles that are also used to accent windows and doorways in the tasting room.

Towns Along the Trail

Both wineries are located near the Town of Colonial Beach, home to a number of local-themed LOVEworks, including a golf cart on the beach, an osprey-themed love sign, and several at area businesses. Local artists are working on more LOVEworks, in an effort to become the Virginia municipality with the most.

Hometowns of other Trail members also have LOVEworks signs reminiscent of their area. Kilmarnock, for example, is home to Trail members Ditchley Cider Works and Good Luck Cellars. Here you’ll find a permanent LOVEwork highlighting the largest industries in the town, and a holiday-themed LOVEwork that is displayed October through December. Look for additional LOVEworks nearby, only minutes from The Dog and Oyster and Jacey Vineyards.

Find the largest LOVE mural in the Tappahannock region, home to Caret Cellars, which is represented by a second mural that includes wine grapes in its design. Located just over the Rappahannock River are Trail wineries Good Luck Cellars and Rivah Vineyards. In this region, four more LOVEworks can be found nearby, in the towns of Warsaw and Montross.

Hope & Glory Inn
Hope & Glory Inn

The Most Romantic Lodging on the Chesapeake Bay Wine Trail

Described as “hopelessly romantic”, “whimsical” and “magical”, Hope & Glory Inn, home to Trail winery The Dog and Oyster, is named one of the Top Ten Most Romantic Inns by American Historic Inns. The boutique inn is made for lovers, featuring seven private guestrooms and six individual cottages, the latter immersed in a “secret garden” with sculptures, a saltwater pool, and a romantic, open-air, outdoor, garden bath. Guests can sip wine from The Dog and Oysters microvineyard and feast on oysters and other farm-to-table and boat-to-table locally sourced foods at the inn’s fine dining restaurant, The Colonnade. The inn even owns a boat called True Love!

Love & Marriage

If love has led to engagement, consider a winery wedding on the Chesapeake Bay Wine Trail. Whether the couples’ preference is luxurious and sophisticated, rustic and homey, or something in between, brides and grooms are sure to find the perfect venue for their nuptials.

Weddings at Jacey Vineyards
Weddings at Jacey Vineyards

Nearly every Trail winery has event-hosting capabilities, for every taste and budget.

  • Hold an Italian-styled wedding at Caret Cellars’ Italy-inspired Tasting Room.
  • The lawn, Manor House, and water’s edge can be used for weddings, rehearsals or accommodations at Ditchley Cider House.
  • The Chef at The Dog and Oyster’s romantic Hope & Glory Inn (see above) can serve formal plated, casual food stations, oyster or seafood bars in the restaurant, on the grounds, or by the pool.
  • Step back in time and say “I do” in General’s Ridge Vineyard’s historic Manor House, Carriage House, or against the breathtaking backdrop of the vineyard.
  • Good Luck Cellars boasts 4,500 sq. ft of indoor space (including a cupola with 360 degree views of the estate), 3,000 sq. ft. of covered, wrap-around porch, and surrounding acreage for weddings.
  • A European-style courtyard with fountain, romantic Barrel Room, indoor/outdoor Pavilion, and dedicated wedding staff are just a few reasons Ingleside Vineyards is an award-winning wedding venue.
  • Guests can arrive by car or boat to Jacey Vineyards for weddings in wooded forests, along a mile of waterfront, and among lush vineyards.
  • Monroe Bay Winery’s Straw Bale Barn and Event Center provides a rustic, yet elegant setting, with shimmering stained glass made from recycled wine bottles, and acres of lawn.
  • Each Tuesday, Rivah Vineyards at the Grove welcomes engaged couples to tour the grounds and meet potential wedding vendors. The winery is also the site for the 2nd Annual Northern Neck Middle Peninsula Wedding Expo Sunday, March 10, 2024.

Gifts That Say “I Love You”

Virginia is for Wine Lovers, a bottle (or case!) of Virginia wine makes a welcomed gift for those you care about. Or go a little extra and say “I love you” with a collection of wine-themed gifts, such as a bottle, wine glass and accessories, and apparel (hat, hoodie, t-shirt, etc.) from a favorite winery. Or go all the way and plan a wine weekend getaway! Visit the Itineraries page on our website for lodging suggestions, attractions, dining and more on or near the Chesapeake Bay Wine Trail.

More personal items, such as jewelry, art or handmade crafts can be found during Trail and individual winery events. Visit our blog post 15+ Places to Shop on the Chesapeake Bay Wine Trail for more gift and shopping ideas.

Share This Post!