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What’s New in Talbot County 2026 | Dining, Events & Waterfront Fun
Discover what’s new in Talbot County, Maryland in 2026—from acclaimed dining and waterfront experiences to new exhibits, events, and places to stay.
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A Maritime Themed Tour of Talbot County
Defined by 600 miles of coastline, Talbot County’s modern seafaring lineage hails back to 1694. Is was then that Talbot County’s first town, Oxford was mandated by Maryland legislation to become the Eastern Shore’s first port-of-entry. The town gained significant prominence as a result and remained a booming port of call for vessels from all…
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Cruisin’ the Great Talbot County Loop
The Great Talbot County Loop – It’s here you’ll find the best of the Chesapeake culture and cuisine, much of it bound together by a ribbon of backroads that string together the small-town pearls of Easton, Oxford, St. Michaels, and Tilghman Island.
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Cruisin’ the Great Talbot County Loop: Stop 4 – Tilghman Island
Route 33 South takes you to the quintessential historic American waterfront village of Tilghman Island. This 20-minute drive is an experience unto itself. Just off the beaten path, Tilghman Island is nestled between the Chesapeake Bay and the Choptank River.
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Cruisin’ the Great Talbot County Loop: Stop 3 – St. Michaels
Nestled along the Miles River, St. Michaels is a historic waterfront town that’s home to museums and boutiques, gourmet restaurants and crab shacks, and plenty of adventure by land or by sea.
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Cruisin’ the Great Talbot County Loop: Stop 1 – Easton
Easton is as sophisticated as it is lively. Featuring a worldclass theater, renowned art galleries, and impeccably curated museums, Easton is the heart of the Eastern Shore’s arts and culture scene.
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Cruisin’ the Great Talbot County Loop: Stop 2 – Oxford
The picture-perfect town of Oxford offers a graceful waterfront and is home to brick-lined streets anchored by history and great restaurants.
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What’s New in Talbot County, Maryland: Attractions, Art, Shopping, and Accommodations
Talbot County, Maryland, is gearing up for an exciting 2025! Find out what’s new in Talbot County – from fresh dining experiences to new attractions, an expanded art scene, to shopping options, and renovated accommodations.
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Experience a Tilghman Island Christmas in 2025
Tilghman Island offers a peaceful and scenic backdrop for the holidays, where visitors can enjoy the natural beauty of the Chesapeake Bay alongside local holiday charm.
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Ring in the Holidays in St. Michaels
The historic, waterfront town of St. Michaels transforms into a magical Christmas village during the holiday season, offering activities, shopping, and waterfront charm to make your festive visit unforgettable.
