Wineries & Waterfront Views: Your Guide to the Chesapeake Bay Wine Trail

There’s something special about pairing a glass of Virginia wine with a waterfront view.

In Virginia’s Northern Neck, visitors can do exactly that. From award-winning vineyards and scenic tasting rooms to winding country roads and Chesapeake Bay vistas, the region offers a wine experience unlike anywhere else in the Commonwealth.

If you're planning a getaway to Montross, VA, spending a day exploring the Chesapeake Bay Wine Trail is one of the best ways to experience the area's beauty, history, and local flavor. Even better? The Inn at Montross serves as the perfect home base for your wine country adventure.

Whether you're planning a romantic weekend, a girls' getaway, or simply a relaxing escape from the city, here's how to build the perfect day exploring the Chesapeake Bay Wine Trail.

What Is the Chesapeake Bay Wine Trail?

The Chesapeake Bay Wine Trail is a collection of wineries located throughout Virginia's Northern Neck and surrounding Chesapeake Bay region. The trail showcases locally owned vineyards that produce a wide variety of wines while offering visitors stunning views, welcoming tasting rooms, and a true taste of coastal Virginia.



Unlike larger wine destinations that can feel crowded and commercialized, the Chesapeake Bay Wine Trail offers a more relaxed and intimate experience. Visitors can enjoy scenic drives, waterfront landscapes, and conversations with the people who grow and craft the wines they serve.

Start Your Day at The Inn at Montross

Before heading out to the wineries, begin your morning with a complimentary breakfast at The Inn at Montross.

Located in the heart of historic Montross, the inn combines 19th-century charm with modern comforts, creating the perfect setting for a relaxing Northern Neck getaway. Guests enjoy cozy accommodations, welcoming common spaces, and a convenient location near many of the region's most popular attractions.

After breakfast, you're just a short drive away from some of the area's most celebrated wineries.

Stop One: Ingleside Vineyards

One of Virginia's oldest and most respected wineries, Ingleside Vineyards offers a classic wine country experience in the heart of the Northern Neck.

Set on a beautiful estate surrounded by vineyards and rolling countryside, Ingleside has earned a reputation for producing award-winning wines while maintaining a welcoming atmosphere for visitors.

Guests can enjoy:

• Wine tastings
• Vineyard views
• Historic grounds
• Seasonal events
• Outdoor seating areas



Whether you're a longtime wine enthusiast or simply looking to enjoy a relaxing afternoon, Ingleside is an excellent place to begin your Chesapeake Bay Wine Trail journey.

Stop Two: General's Ridge Vineyard

Located in nearby Hague, General's Ridge Vineyard combines handcrafted wines with a peaceful rural setting.

The property features beautiful scenery, a welcoming tasting room, and a diverse selection of wines that appeal to a wide range of palates.

Many visitors appreciate the relaxed atmosphere and slower pace, making it an ideal stop for couples and groups looking to enjoy an afternoon in Virginia wine country.



Highlights include:

• Local wines
• Scenic countryside views
• Seasonal events
• Outdoor gathering spaces

Stop Three: The Hague Winery

For those seeking a unique and memorable stop along the trail, The Hague Winery offers exceptional wines and a charming waterfront setting.

The winery's location reflects everything visitors love about Virginia's Northern Neck: beautiful scenery, small-town hospitality, and an appreciation for local craftsmanship.



Visitors can enjoy:

• Wine tastings
• Waterfront views
• Relaxed outdoor seating
• Special events throughout the year

Pair Wine Tasting with Northern Neck Exploration

One of the best things about exploring the Chesapeake Bay Wine Trail is that it naturally connects visitors to many of the region's most popular attractions.



While you're in the area, consider adding:

Stratford

Hall

The birthplace of Robert E. Lee and one of Virginia's most significant historic landmarks.

Westmoreland State Park

Known for scenic hiking trails, waterfront views, & fossil-rich beaches along the Potomac.

Historic MONTROSS

Browse local shops, dining, & experience the charm of one of Virginia's most welcoming towns.

Why Stay Overnight Instead of Driving Home?

One of the biggest mistakes visitors make is trying to squeeze the Chesapeake Bay Wine Trail into a single-day trip.

The Northern Neck is meant to be enjoyed at a slower pace.

By staying overnight at The Inn at Montross, you can:

• Enjoy multiple winery stops without rushing
• Explore local attractions at your leisure
• Experience Montross after the day visitors leave
• Relax with daily happy hour at the inn
• Wake up to a complimentary breakfast the next morning



Instead of watching the clock, you'll have the freedom to truly enjoy everything the region has to offer.

Planning a Romantic Getaway or Weekend Escape?

The Chesapeake Bay Wine Trail is one of the most popular experiences for couples visiting Virginia's Northern Neck.

Picture your day:

• Breakfast at the inn
• Vineyard visits and wine tastings
• Scenic drives through the countryside
• Waterfront sunsets
• A cozy evening back at The Inn at Montross

It's the kind of getaway that feels both relaxing and memorable.

Make The Inn at Montross Your Wine Country Home Base

Whether you're discovering Virginia wine for the first time or returning to explore new vineyards, the Chesapeake Bay Wine Trail offers an unforgettable way to experience the Northern Neck.

And when it comes to where you stay, location matters.

The Inn at Montross places you near the wineries, attractions, waterfront views, and small-town charm that make this region so special.

Your perfect wine country getaway may be closer than you think.