Where to Pop THE Question

The natural beauty of the landscape, the charming historic towns, and of course, the stunning waterfront make Talbot County the perfect backdrop for popping the question—and saying I do.  Here are a few ways to make this moment extraordinary.

Anchors Away: Selina II

Ask for her (or his) hand under raised sail on the Chesapeake Bay. The Selina II, a skippered 1920s yacht, offers a special engagement package that takes the stress out of the proposal. The boat can accommodate six people, but it is cozy enough for two.
101 North Harbor Road, St. Michaels | 410-726-9400

First Kiss: Honeymoon Bridge

Stroll along the small pedestrian bridge known as Honeymoon Bridge, Sweetheart Bridge, or sometimes, Lovers’ Bridge. This site has been a couple’s favorite since the golden age of Hollywood when Gary Cooper and Fay Wray shot a romantic scene here in the 1935 film “The First Kiss.”  Have your own first kiss as an engaged couple in the very same spot.  Today the bridge, which is festooned with colorful flower baskets in warm weather, is also a favorite site for wedding—and engagement – photos.
102 Cherry Street near Navy Point, St. Michaels

Love at First Flight: Easton Aviation

Take in the beauty of the Chesapeake Bay and the pristine landscape of the Eastern Shore by soaring in the sky high above on a Cessna Skyhawk, a sleek single-engine plane, with Easton Aviation. Departure is easy breezy from Easton Airport. The pilots can even help you design your own route to swoop over places that hold special meaning to you both.
Easton Aviation, Easton Airport, 29137 Newman Road (just off Route 50), Easton | 410-822-8181

On Top of the World: One Couple’s Fairytale Proposal

Talbot County has many unique places to propose. When Weston Anderson was looking for a one-of-a-kind place to propose to his girlfriend Jillian, he chose the Avalon Theatre, an Art Deco gem that’s the hub of cultural life in Talbot County. He arranged to bring her up to the wraparound balcony on the top floor of the theater that overlooks downtown Easton, invited a few of her close friends to surprise her (and take photos) and the rest is history. (She said yes!)

“I value Jillian above all else in the world and meeting her was the apex of my life. After spending time together at a holiday work party at the Avalon Theatre, I knew I wanted to spend the rest of my life with her. When I decided that I was going to ask her to marry me, I was sure that I had to propose at the Avalon since it is literally and figuratively the highest point in town. It’s humbling to think of all the people who have come through these doors over the past 100 years, and we love that we are a tiny piece of the theater’s history.”

Privacy Perfected: The Inn at Perry Cabin

The Inn at Perry Cabin has a fleet of extraordinary boats that depart right from the resort’s dock. You can book a yacht for an hour, a full day or anything in between. Best of all, the captain can ferry the two of you to an uninhabited island or a secluded cove where you will feel like you are the only people in the world. Pro Tip: Bring your swimsuits and take a post engagement dip.
308 Watkins Lane, St. Michaels | 410-745-2200

Knapps Narrows Bridge to Tilghman Island in Talbot County, Maryland.

Beauty of the Bay: Views of Chesapeake Bay from Tilghman Island

Cycle or drive to a small beach and rocky promenade on Tilghman Island for majestic views of the Chesapeake Bay. If timed right, you can capture one of the finest sunsets in the world. The photogenic Sharps Island Light, a cast iron lighthouse built in 1938, sometimes compared to the Leaning Tower of Pisa thanks to its tilt, adds to the distinctive charm of the backdrop.
On the eastern side of Black Walnut Road, toward the very end of Tilghman Island

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