Mark’s Score 8.7
St Michaels is perhaps the most popular tourist destination on the bay side of the Delmarva. It is also one of Delmarva’s most upscale tourist destinations. Its close proximity to the wealthy suburbs around Washington, its ample marina capacity, its quiet coves, its historic charm, and its many upscale restaurants and shops make it a favored destination for the well-off tourist.
St Michaels is young by Delmarva’s standards. It was first settled in the 1770s and was not incorporated until 1804. In the early 1800s it became a center of ship building with as many as six active shipyards by 1812. The St Michaels’ shipyards were famous for constructing Baltimore Clippers. The clippers were famous for being sleek, fast, and maneuverable and were designed to evade blockades, and outrun naval vessels and pirates. It was the presence of these shipyards that caused the British Navy to bombard the town in the War of 1812. Legend has it that the locals fooled the British Navy into bombarding the wrong location by hanging lanterns in trees outside of town. Whether true or not, both the town and shipyards managed to survive the bombardment relatively unscathed, and the town gained the nickname, “the town that fooled the British.”
St Michaels is located on a narrow isthmus between the Miles River and Broad Creek, meaning no matter where you are in town you have water vistas, and endless opportunities for multiple water activities. Given that it is on a narrow isthmus, the town is small in area and everything is within an easy walk. If you holiday here, you can park your car in the hotel parking lot and never enter it again until you leave
In many ways St Michaels reminds me of Nantucket. It has that same upscale tourist vibe while remaining true to its historical past. Having said that, I find Talbot Street (the main street in town) to be just a bit too touristy, and a bit too Disneyesque. The real charm of the town can be found on its side streets, where you will find many buildings from the 18th and 19th centuries, not to mention multiple small bays full of sailing craft. So, while Talbot Street may border on Disneyland, all you need do is walk one block to the left or right of Talbot to find a charming early American village with spectacular water views. You need only wander a few blocks to understand why St Michaels became a tourist destination.
For me, the real charm of the town rests on the streets hard by the harbor, Carpenter, Locust, Cherry, Mill, and Green. If you are not in town at the height of summer, you could almost feel you were back in the early 1800s when walking these streets. If you really want to experience the full charm of this town, visit in the off season.
Places rated in or near St.Michaels
| Rating Date | Place | Category | Score |
| 2024 Nov | Chesapeake Maritime Museum | Museum | 9.43 |
| 2024 Dec | The Fool’s Tavern | Restaurant | 9.04 |
| 2025 Feb | Ava’s Pizzeria | Restaurant/Pizza | 9.04 |
| 2024 Dec | Windon Distillery | Shop/Liquor | 9.03 |
| 2024 Oct | Village Shoppe | Shop/Providore | 8.80 |
| 2024 Oct | Bordeleau Vineyard | Shop/Wine | 8.73 |
| 2025 Jan | Eastern Shore Brewery | Craft Brewery | 8.41 |
| 2025 Feb | St Michaels Winery | Shop/Wine | 8.28 |
| 2024 Aug | Limoncello | Restaurant | 8.04 |
| 2024 Nov | Foxy’s Harbor Grille | Restaurant/Bar | 7.84 |
| 2024 Oct | Carpenter St. Saloon | Restaurant/Bar | 7.62 |
| 2024 Nov | Sprout Cafe | Restaurant/ Coffee | 7.28 |
| 2024 Sep | Talbot St. Tavern | Restaurant/Bar | 7.15 |
Places reviewed in or near St Michaels
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