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Best 5 Towns to Live in on the Eastern Shore

St. Michaels HarborThe Eastern Shore of Maryland is a wonderful place to live. There are many towns to choose from, resting in the nine counties east of the Chesapeake Bay. There are twenty three towns to choose from in Talbot County, Queen Anne’s County, and Caroline County alone…all with their unique individual charms and history. 

Talbot County has been called the “Hamptons of the Eastern Shore”. The 600 miles of shoreline once provided harbor to working fishing boats and has since become a paradise for the recreational boating community. 

Queen Anne’s County is home to many charming waterfront towns and thousands of acres set aside for recreational opportunities in over twenty parks. Queen Anne’s County Parks and Recreation works with residents and businesses to enhance and maintain natural resources with careful planning and development initiatives, strengthening the local economy and providing opportunities for all. 

Caroline County is a nature lover’s paradise with 8,000 acres of nature preserves, wildlife sanctuaries, and parks to explore. There are two championship golf courses to play and canoeing, kayaking, fishing, and bird-watching to enjoy all summer long. 

Here are five of the best towns to live in on the Eastern Shore (on the eastern side of the Chesapeake Bay). 

1. Easton: This historic town in Talbot County has been recognized as one of the best small towns to live in by Budget Travel Magazine. The town was incorporated in 1790. Walking along the street in the town center will evoke the Victorian and Colonial charm of yesteryear in a thriving community of 16,000+ people. The town hosts the Chesapeake 

Film Festival in September, the Academy Art Museum Craft Show in October, and a Waterfowl Festival in November. There is an Amish Country Farmers Market Thursday-Saturday and the Easton Farmers Market on Saturday for all of your locally grown produce needs and artisan wares. You can enjoy a relaxing day at Pickering Creek Audubon Center, a 400 acre working farm, searching for Monarch butterflies in the sanctuary during their annual migration from Mexico in September among other seasonal events. Explore homes for sale in Easton, MD. 

2. Centreville: This Queen Anne’s County town is full of history and small town charm. The town was incorporated in 1794. The 18th century courthouse is still in use. It was completed in 1792 with four rooms but remodeled in 1876 to provide additional space. The building draws visitors with historical interest, and perhaps a little interest in the ongoing daily court proceedings. The town has a population of 5,000+ people, and they recognize the importance of agriculture past and present. The Queen Anne’s County 4-H Park was opened in Centreville in 1942 with a deed reading “for the use only for agricultural activities with 4-H Club work preference”. The park is home to the annual country fair which will celebrate its 80th anniversary from August 8th-13th 2022. Explore homes for sale in Centreville, MD. 

3. Ridgely: The “Dream Town” of Ridgely in Caroline County was established in 1867. It was originally planned to be a large city during the railroad boom following the American Civil War. Four buildings were completed, but the developers went bankrupt. The town remained small. The current residents love the sense of community that comes with a population of 1,600+ people. There is the annual Strawberry Festival, complete with the Strawberry Festival Parade to enjoy. There are plenty of youth activities including lacrosse, soccer, baseball, football, 4-H, and dance. A trip to the Adkins Arboretum delights visitors every season of the year with guided walks, bird-watching, plein air painting, tea in the trees, and a beer garden. The town is known for its Victorian homes and family friendly events. Explore homes for sale in Ridgely, MD. 

4. St. Michaels: This quaint harbor town in Talbot County took its name from the parish established there in 1677. The church attracted settlers skilled in shipbuilding and the tobacco trade. The town was incorporated in 1804. The population of just over 1,000 people enjoys life in what USA Today recognizes as one of America’s “Top 10 Best Small Coastal Towns”. There are wine festivals, oyster festivals, fine art galleries, estate and fine jewelry shopping, and unique boutiques. The dining is exceptional and many restaurants have amenities specific to dogs, as the town takes pride in being dog friendly. This is the perfect coastal town to enjoy bicycling, sailing, and kayaking. There is a variety of real estate to explore, including properties dating back to the 1600s. Explore homes for sale in St. Michaels, MD. 

5. Oxford: This town in Talbot County was laid out in 1683 and incorporated in 1852. The current population of 600+ people enjoys a quiet and charming quality of life on the waterfront. The Oxford Community Center provides a gathering spot for meetings, classes, lectures, and dinner theater in a 1928 brick schoolhouse. You can gather a colorful and illustrated sense of the community by visiting the Oxford Community Center YouTube channel. Art exhibit reviews, musical performances, studio tours, and the popular “Cooking with Larry” series are a great way to meet your new neighbors and dial in a tasty paella or shrimp and grits meal for the family. Explore homes for sale in Oxford, MD. 

We look forward to helping you and your family find the perfect home on the Eastern Shore. Contact Chuck Mangold today!

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