Trails, Seafood and Tastings in Queen Anne’s County, Maryland

Food & Beverage, Northeastern US Itinerary


Spend three days in Queen Anne’s County with the Chesapeake Bayas your backdrop and experience trails,waterfront dining, wineries, breweries and exceptional views.


Enjoy great waterfront views in Queen Anne’s County.

Enjoy great waterfront views in Queen Anne’s County.

Enjoy These Great Maryland Attractions and More:

  • Dock House Restaurant
  • Stop by the Chesapeake Heritage & Visitor Center
  • Visit Matapeake Clubhouse and Beach
  • Visit Dessert First in Kent Narrows
  • live music at Red Eye’s Dock Bar or The Jetty
  • Chesapeake Bay Environmental Center



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The Chesapeake Bay is a great place to enjoy beautiful scenery.

The Chesapeake Bay is a great place to enjoy beautiful scenery.



Start your visit with fresh Maryland seafood. Dock House Restaurant, Chester or Harris Crab House, Grasonville both offer great waterfront views of the Kent Narrows and savory fresh seafood.

Stop by the Chesapeake Heritage & Visitor Center. Museum space is dedicated to the history, heritage, and culture of the area. While there, take a walk out to Ferry Point Park.

Next, enjoy the trail system. The Cross Island Trail and the South Island Trailare flat and friendly for all levels of walkers, runners, and bicyclists offering exceptional views as it traverses through marshes, farms, and wooded areas. Each trail is about 7 miles long!

If you don’t want to walk the entire trail, you can still enjoy some of the highlights by making a few short trips. Visit Terrapin Nature Park and enjoy the view from the living shoreline of this 276-acre nature preserve. If you’d like to explore further visit Matapeake Clubhouse and Beach and enjoy the beach access and South Island Trail.

Check into The Inn at Chesapeake Bay Beach Club, Maria’s Love Point Bed & Breakfast or one of the area’s flag hotels to relax and refresh.

Next, enjoy wine tasting and expansive views of the vineyards at Love Point Winery and Cascia Vineyards.

Tonight’s dinner is at Libby’s Coastal Kitchen and Cocktails or Kentmorr Restaurant & Crab House. Both offer menus with locally sourced seafood served in a Bayfront setting.


Visit Dessert First in Kent Narrows and take a quick walk with coffee in-hand while getting fresh air and the beautiful views.

There are plenty of options for exploring Queen Anne’s County from the water. More than a dozen charters provide anglers in your group with the Chesapeake Bay sport fishing experience. Maryland Fishing and Hunting, LLC offers excellent charters with catering and Good Time Charterhas a chef on board for fresh, home cooked meals. Book in advance with one of our many charter boat options.

Enjoy a brewery tour this afternoon. Start with Cult Classic Brewery, they have 15+ beers brewed in house on tap. Next, it’s Patriot Acres Brewery on the north end of the county. Enjoy the farm animals, farmland views and play a few games of cornhole. Then head to Bull & Goat Brewery and Old Courthouse Distilling and enjoy their taproom and shuffleboard. Finish your afternoon with Ten Eyck Brewery. Enjoy the relaxed atmosphere, handcrafted beer, cider, and homemade non-alcoholic sodas. If you’re not up for a full tour just pick one brewery and enjoy!

Return to your host hotel to relax and refresh before grabbing dinner.

Enjoy one of many waterfront dining options such as Fisherman’s Inn, family owned since 1930, or Bridges on Kent Narrows. Make sure to sample fresh crabs or oysters if they’re in season when you visit.

Wind down by catching some live music at Red Eye’s Dock Bar or The Jetty. 

 DAY 3

Have breakfast and checkout of your hotel and depart for the Chesapeake Bay Environmental Center (CBEC) and explore the many self-guided tour options such as Hummingbird and Butterfly Garden Exploration or themed hikes on the 510-acre preserve. Make sure to see the Bird of Prey Outdoor Exhibit.

Do allow some time this morning for shopping at local shops, antique stores, and outlets.

Enjoy lunch before departing Queen Anne’s County.

Grab a copy of our visitor’s guide to start planning your next trip.

Maryland still has plenty more for travel groups to experience, so be sure to Subscribe to Leisure Group Travel for FREE and get even more travel ideas and tips

Destination Client Name

Queen Anne’s County

April Plummer


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