Affordable Waterfront Resort Living

Affordable Waterfront Resort Community in Virginia Maryland

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Small Town Charm for the Holidays

Dec 08, 2014

The holidays are a great time of year to explore small towns and take in all the charm that goes with them! Enjoy the rich history, support local business while shopping and taking in a meal or two and marvel at the slower pace you're able to enjoy life. We've highlighted 5 local eastern shore towns for you to explore below.


The Friendliest Town on the Eastern Shore! Take in a movie or a show at The Historic MarVa Theater, capture the very essence of Pocomoke's history with a tour of The Delmarva Discovery Center and learn about what makes Pocomoke City and the surrounding areas so very special. Visit one of their two museums rich in local flavor, The Sturgis One Room Schoolhouse and The Coston House.


The waterside community of Crisfield in Somerset County, MD is the southernmost town in Maryland. Located on the Eastern Shore of the Chesapeake Bay, Crisfield is famous for its seafood - especially the Maryland blue crab - its Watermen, wildlife, natural beauty, simple lifestyle and strong sense of community built on faith and hard work.

Cape Charles:

Located on the shores of the Chesapeake Bay, Cape Charles continues its amazing transformation, recapturing its 1880s glory days when the railroad gave birth to this post-Victorian beauty. B&Bs, a boutique hotel, and cottage/resort rentals make staying here a pleasure. Unique shops in the downtown area, a full service European day spa, and nearby guided horseback trail rides on a waterfront estate add to the offerings. Dining includes waterfront restaurants, a Viennese-inspired coffee house, Irish pub, old-fashioned soda fountain, and more. The Cape Charles Museum provides a fascinating look back in time to see how Cape Charles was formed.

Even though this video is geared towards seasons other than winter (you can always plan ahead),
we loved it and wanted to share it.

*If you'd rather visit by sea, we've also shared local boating destinations to visit that might interest you!


Onancock is a small waterfront town on the Eastern Shore of Virginia offering shopping (lots of antiques), dining, bed and breakfasts and more!

Tangier Island:

Tangier Island, dubbed the "soft crab capital" of the nation, is a unique island located in the middle of the Chesapeake Bay. If you would like to see an unspoiled fishing village with quaint, narrow streets, then take a step back in time and visit Tangier Island today! The people of Tangier, who speak with a lingering trace of Elizabethan accent, are warm, friendly and proud of their island. They live here because they like the lifestyle and have no desire to live on the mainland. Spend some time on Tangier. Visit by air or sea. Stay for the night in one of the delightful bed and breakfasts, or take a day-trip on one of the ferries. An experience on Tangier Island will stay with you for years to come. It might be small in population, but the people of Tangier have a great love of the Chesapeake Bay and each other.

These are just some of the many small towns near Captain's Cove. Whenever you make the trip, enjoy the visit!