The Hamptons of the mid-shore, people have been seeking out St Michaels for years falling in love with the cute downtown and delicious restaurants, as well as seeking solace from the hustle and bustle of the city in the many waterfront estates that kiss the outskirts of the town. Keeping that small town feel with locally owned and operated businesses within the town, and keeping the major franchises and conglomerates out, this town is perfect year-round for the many locals, as well as the weekenders and vacationers. Delicious restaurants sprinkled along the waterfront have access via the water and the road.
The historical seat of Caroline County is located on the Choptank River. A tight-knit small town feel where the locals welcome you with a smile. Conveniently located with easy highway access to head towards the beaches or Washington DC. The community organizers tirelessly work to provide residents with all types of festivals, parades, farmers' markets, and more. Agriculture is huge here, so depending on whether you want those water views or wistful farm views, Denton has something for everyone.
This arts and cultural-centered small town have been voted 8th Best Small Town in America. Tony brick buildings full of character make up this sophisticated center of the Eastern Shore. Get lost wandering into all the unique small business shops and beautiful homes that make up Downtown Easton. Living in town, one would never run out of things to do and the walkability makes it a very desirable area to live. Chesapeake Bay tributaries offer Talbot County over 600 miles of waterways and 27 public landings.
Looking for a little more relaxation. One of the only towns on the Shore that has a public beach, this little hamlet has been a local haunt for years. Delicious restaurants dot the waterfront that can accommodate boats and cars alike. And don't forget, the best months for fresh oysters are the months that end in "-ER"