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Kellen & Kieran

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Things To Do

Hi Friends and Family, Historic Kent Island Resort is located on the shores of the Chesapeake Bay. Surrounded by numerous waterfront activities and restaurants, as well as being located with 25 minutes of downtown Annapolis, the area offers a variety of things to do in your free time. We have listed a few activities and local eateries nearby. Love, Kieran & Kellen

Blue Heron Golf Course

3270 Romancoke Road, Stevensville, MD 21666
, (410) 643-5721

Queenstown Harbor Golf

310 Links Lane, Queenstown, MD 21658
, (410) 827-6611

United States Naval Academy Golf Club

64 Greenbury Point Road, Annapolis, MD 21402
, (410) 293-9747

Sandy Point State Park

1100 East College Parkway, Annapolis, MD 21409
, (410) 974-2149

Gorgeous park on the water with beautiful trails and water activities. This is actually the location we had our engagement photos taken.

Naval Academy

121 Blake Rd, Annapolis, MD
, (410) 293-1000

Love Point Vineyards and Winery

305 River Shore Lane, Stevensville, MD 21666
, (443) 786-2765

Chesapeake Bay Sport Fishing

337 Pier 1 Road, Stevensville, MD 21666
, (443) 347-4464

Good Time Charters

412 Congressional Drive, Stevensville, MD 21666
, (410) 739-9977

Fishing, dining, crabbing, and cruising. Take your pick. Check out all of their packages aboard their charters.

Annapolis Waterfront

1 Dock St, Annapolis, MD 21401

Downtown Annapolis has tons to offer! It has several waterfront restaurants and shops to include Choptank, Carrol's Creek Cafe, Chart House, Annapolis Ice Cream Company, Osteria 177, Federal House Bar & Grille, Annapolis Market House, Pusser's Caribbean GrilleDock Street Bar & Grill, McGarvey's, and much much more.

Chessie’s Wharf

609 Melvin Avenue, Annapolis, MD 21401
, (443) 603-1235

Local Maryland brewery that offers outdoor seating, a variety of beer, wine, and liquor, is pet friendly and has delicious smash burgers.

Carrol's Creek Cafe

410 Severn Avenue, Annapolis, MD 21403
, (410) 263-9102

We go to this restaurant to celebrate all of our milestones, including our engagement. It's an elegant waterfront seafood restaurant overlooking Spa Creek & serving classic Chesapeake fare.

Chart House Prime

300 Second Street, Annapolis, MD 21403
, (410) 268-7166

High-end chain eatery serving seafood & steakhouse fare in a classy setting with views. This is actually the restaurant we took my parents the first time they met Kieran.

Boatyard Bar & Grill

400 Fourth Street, Annapolis, MD 21403
, (410) 216-6206

Vibrant nautical-themed spot for crab, oysters & other seafood, plus burgers, pizza & a full bar. One of Kieran's favorite local restaurants. It's one of the first places we go to to celebrate family birthdays or meet up with friends. Hands down the best orange crushes in town!

The Jetty

201 Wells Cove Road, Grasonville, MD 21638
, (410) 827-4959

Overlooking Kent Narrows, this bar & grill offers pub fare & seafood, plus live music on weekends. This is also the location of our Welcome Party that will take place around 7:00pm on Friday, October 10, 2025.

Dock House

110 Piney Narrows Road, Chester, MD 21619
, (443) 446-4477

Enjoy panoramic views of the Kent Narrows, amazing food, signature cocktails and wines from inside our restaurant, or enjoy outdoor seating on our wrap-around deck.

The Big Owl

3015 Kent Narrow Way South, Grasonville, MD 21638
, (410) 827-6523

Airy hangout set on a dock, offering 3 bars, elevated pub fare & seafood, plus weekend live music.

Bridges Restaurant on Kent Narrows

321 Wells Cove Road, Grasonville, MD 21638
, (410) 827-0282

Waterfront American restaurant known for seafood, small plates & pizza plus a full bar, deck & dock.

Libbey's Coastal Kitchen and Cocktails

357 Pier 1 Road, Stevensville, MD 21666
, (410) 604-0999

Located on the Chesapeake Bay at the base of the Bay Bridge, Libbey's Coastal Kitchen + Cocktails is the perfect place to enjoy breathtaking views, gorgeous sunsets , fresh local seafood and hand crafted cocktails.

For all the days along the way
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