Talbot County, once known for its working watermen making their living on the Chesapeake Bay, has now become a paradise for boaters, and a haven to relax, shop and explore. With over 600 miles of shoreline it’s dubbed the “Hampton’s of the Eastern Shore”.

There’s charming Tilghman Island, Oxford with its Colonial roots, St. Michaels with its alluring blend of old and new and the historic town of Easton named as one of the best small towns in America by Budget Travel Magazine.

Enjoy an exhilarating cruise on a historic skipjack. Explore the Chesapeake Bay Maritime Museum, with fun-filled maritime festivals and exhibits of exceptional workmanship of wooden boat builders not to mention sailing, fishing and biking.

If it’s wineries you want, Little Ashby Vineyards is located on the banks of the Miles River. The winery can be reached by boat as well as by car or bicycle. Movies like The Wedding Crashers and Failure to Launch were filmed here.

Easton has a booming arts scene including Delmarva’s premiere art museum- The Academy Museum. Talbot has three championship golf courses including Hog Neck, rated one of the top 25 public courses in the country.

Cities in Talbot County, Maryland include: Easton, St. Michaels, Sherwood, Fairbank, Oxford, Trappe

Top Ten Things to Do in Talbot County

1. Chesapeake Film Festival – September 18-20, Downtown Easton.
2. Academy Art Museum Craft Show – October 10-11- is the Eastern Shore’s largest juried craft festival.
3. Concours d’ Elegance – September 27, 2009.
4. Go Wild at Easton’s annual Waterfowl Festival November 13-15.
5. Mid-Atlantic Small Craft Festival – October 31.
6. 12th Annual Boating Party – September 12.
7. 12th Annual Boat Auction – September 5.
8. Tilghman Island Day – October 17. A day of heritage celebration, great seafood, good music and fun.
9. Fall into St. Michaels – October 30- November 1. Parade, costume contests, pumpkin-carving contest, ghost tours and lots of hair-raising haunt fun.
10. Traditional Oxford Fence Art Sale -October 10. Oxford residents used the Traditional Oxford Fence to share their artistic talent.