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Leah & Jared

April 25, 2026
7 Days To Go!

Leah & Jared

April 25, 2026
7 Days To Go!

Things to Do

We both grew up in Maryland and love nothing more than to show you some of the places we think are so special. You can relax by the water at a park or drive over the Bay Bridge to explore Annapolis. Below, you’ll find a list of places to visit and things to do—perfect for anyone who loves to explore.

Chesapeake Bay Maritime Museum

Picture of Chesapeake Bay Maritime Museum
213 N Talbot St, St Michaels, MD 21663, USA
(410) 745-2916

Where Leah's dad purchased his boat this Maritime Museum is exceptionally beautiful and informative. Learn all about maritime history on the eastern shore.

Website

Love Point Vineyards and Winery

Picture of Love Point Vineyards and Winery
305 River Shore Ln, Stevensville, MD 21666, USA
(443) 786-2765

The tasting room is open Thursday-Sunday 12:00-5:00 PM no reservation necessary! No outside food allowed.

Queenstown Harbor Golf

Picture of Queenstown Harbor Golf
310 Links Ln, Queenstown, MD 21658, USA
(800) 827-5257

Queenstown Harbor Golf offers two top-rated public golf courses in Maryland, just a short drive from Washington, D.C., Baltimore, and Annapolis. Set along the Chester River, golfers enjoy panoramic water views, scenic fairways, and newly renovated bunkers designed to enhance playability and challenge. Recognized by Golf Digest and consistently ranked among the best in the region, the courses are known for their pristine conditions and thoughtful layouts. Open to the public year-round, Queenstown Harbor delivers an unforgettable golf experience for players of all skill levels. Book up to 14 days in advance.

Cross Island Trail trailhead

Picture of Cross Island Trail trailhead
113 Jackson Creek Rd, Grasonville, MD 21638, USA
(410) 758-0835

Take a hike! Or a bike ride, or a light jog. Whatever you do try out the 6.5 mile Cross Island Trail to see the beauty of Kent Island. The trail ends at the Terrapin Nature Park, a great place for a picnic.

Ferry Point Park

Picture of Ferry Point Park
425 Piney Narrows Rd, Chester, MD 21619, USA

If you would prefer a shorter walk Ferry Point park located next to the Chesapeake Heritage and Visitors Center has views that can't be beat.

Harris Crab House

Picture of Harris Crab House
433 Kent Narrow Way N, Grasonville, MD 21638, USA
(410) 827-9500

So you've driven to Maryland and you want to eat some crabs? You've come to the right place. Just a short walk from most of the hotels where we have room blocks. Other seafood suggestions include: Bridges and The Narrows.

Chesapeake Water Tours - Kent Narrows

3028 Kent Narrow Way S, Grasonville, MD 21638, USA
(443) 566-3386

Set sail on your very own boat tour! If its warm enough.

Annapolis

Kent Island is just over the Bay Bridge to Annapolis, a great place to explore. However please leave plenty of travel time to your plans as Bay Bridge traffic can be unpredictable.

Preserve

Picture of Preserve
164 Main St, Annapolis, MD 21401, USA
(443) 775-2885

A personal favorite restaurant on the main street in Annapolis

Annapolis Spring Boat Show

Picture of Annapolis Spring Boat Show
110 Compromise St, Annapolis, MD 21401, USA
(410) 268-8828

For just $20 a day attend the Annapolis sailboat show occurring all weekend. Please leave yourself plenty of time while traveling to get over the bay bridge.