Easton – St. Michaels, Maryland

Best Places to Retire in Maryland


Easton (population 11,000) is located on the Maryland’s Upper Eastern Shore – the eastern shore of Chesapeake Bay. It is about the same distance from the Susquehanna River source and as from the Lower Bay where it empties into the Atlantic Ocean. The town is just over 10 miles east of the port village of St. Michaels. http://www.town-eastonmd.com/

Historic Easton, which served as the Colonial Capital of the Eastern Shore, is today the county seat of Talbot County. It has preserved its first building, which was a Meeting House erected in 1682. Easton has been rated as “The 8th Best Small Town In America,” and is among “The Top One Hundred Small Arts Communities in America.”

Easton is a scenic and charming community with a very busy civic and arts calendar. There is live entertainment, casual and gourmet dining, a great deal of specialty shopping, fine galleries, and up-scale shopping. It is a safe town and filled with events such as First Friday Gallery Walks, street music, an old-fashioned Fourth of July with music, carnival rides, and fireworks, and First Night festivities on New Year’s Eve in various parts of town.

And from June until December, there is a Saturday Farmers’ Market with all kinds of produce, flowers, and baked goods. There are plenty of outdoor recreation and sports opportunities, including a great many offered all along the nearby Chesapeake Bay. It is a great place to go for a bike ride or a hike and there are a couple of outstanding golf courses nearby. Historic Easton Town Center offers extensive shopping with everything from “A” for antiques to “W” for waterfowl decoys.

There are clothing stores, specialty shops, music stores, pet shops, photography, riding apparel, books, candles, up-scale boutiques, novelties, fine china and costume or expensive jewelry, sportswear, toys, and much more. St. Michaels (population 1,200) is located on a very protected harbor on the Miles River, a short distance before it reaches the open waters of Chesapeake Bay. It is just over 10 miles due west from Easton.

The history of this well-preserved little port community dates to 1778 when James Braddock first laid it out. In 1813, the British planned an attack on St. Michaels in hopes of confiscating the fastest ships on the sea. Forewarned citizens hung lanterns in the masts of ships and tree tops, tricking the British into firing cannons over the town. Often St. Michaels is referred to as “The Town That Fooled the British.” Today St. Michaels retains some of its early character in its collection of colonial, federal, and Victorian homes, and a number of beautiful old churches.

The town cherishes and celebrates its place in history. http://www.stmichaelsmd.org/

St. Michaels is a popular summer destination and offers a large number of boutiques, clothing stores, jewelry stores, antique shops, sportswear, galleries, and specialty shops. There are ice cream parlors, snack shops, and a good number of restaurants, many which specialize in seafood fresh from local waters. There is a good assortment of B & Bs, inns and hotels, and several marinas that accommodate both residents and the many transient vessels.

The area is widely recognized for its seafood that is shipped on a regular basis to destinations such as Baltimore, Annapolis, Ocean City, Dover, and Washington, DC. There are water sports of all kinds available, including fishing, sailing, power boating, charters, cruising, canoeing and kayaking.

The flat rural roads in the area have wide shoulders and are popular for cycling and horseback riding. There are both indoor and outdoor arenas and riding trails, plus a 36-mile bike route from St. Michaels to Oxford, Easton and back again. In addition, residents and visitors will find two outstanding championship golf courses in the area. The Easton – St. Michaels area offers all of this quality of life — and they are only a short drive from Annapolis, Baltimore, and Washington, DC. It isn’t surprising that the area has been discovered and received such rave reviews. http://www.talbotchamber.org/

Arts & Culture

Chesapeake Bay Maritime Museum is dedicated to furthering an interest and understanding of the maritime culture of the Chesapeake Bay area. It features an 18-acre waterfront setting with 10 exhibit buildings, historic Hooper Straight Lighthouse, an aquarium, a working boat yard, and a collection of over 85 sail, power, and row boats. It also hosts a number of festivals and concerts on the grounds throughout the year. http://www.cbmm.org/

St. Mary’s Square Museum in St. Michaels is open on weekends from May to October. It offers a guided walking tour through the town’s historic streets built in the 18th and 19th centuries. (410-745-9561). The Academy Art Museum of Easton is a fine arts museum established in 1958. It hosts exhibitions and performances as well as visual and performing arts classes for children and adults. http://www.art-academy.org/

Talbot County Arts Council provides funding and support of the arts. http://www.talbotarts.org/

Bay Country Chorus of the Barbershop Harmony Society, Easton Chapter (SPEBSQSA) 

Historic Avalon Theatre is a restored art deco theater in Easton. It presents a wide range of live entertainment year ’round and hosts community and educational events. Performances and events include chamber music, dance, theater, lectures, and well-known entertainers and musicians. 

The Eastern Shore Chamber Music Festival is a decades old annual event that offers six concerts featuring both classical and contemporary music. It also features open rehearsals and concerts in the streets. 

The Waterfowl Festival in Easton during November features art, carving, sculpture and photography. There are decoy auctions, calling contests, retriever, fly-fishing and shooting demonstrations, and more. http://www.waterfowlfestival.org/

The Talbot County Historical Society preserves and supports the history and culture of the county. 

First Night Talbot is an annual New Year’s Eve event in Easton. A family-oriented, alcohol-free community festival, it features indoor and outdoor arts performances throughout the historic downtown areas of Easton. 

Pickering Creek Audubon Center is a 400+ acre site that includes forest, fields and shoreline. It offers a wide range of programs for all ages including lectures, guided field trips, canoe rentals, and more. http://www.pickeringcreek.org/

Jean Ellen duPont Shehan Audubon Sanctuary is a 950-acre preserve in Bozman, Md, nine miles from St. Michaels. It consists of more than eight miles of shoreline and ten miles of trails. The sanctuary features education and outdoor programs for both children and adults. It is open on selected days for biking, hiking, canoeing, kayaking, horseback riding and birding. It also offers mule wagon rides and more. 

Tred Avon Players is a non-profit theater group that performs at the Oxford Community Center. The group, which has been active since 1982, presents plays and musicals. http://www.tredavonplayers.org/

Annual Oxford Day is an event that features a local parade, foot race, dog show and lots of other family fun. It is held the fourth Saturday of April. 


There are outstanding opportunities for all water sports, either on the Chesapeake Bay or on one of the many rivers and inlets and small bays throughout the area. In all, Talbot County boasts over 600 miles of waterfront. There are also great places to bike and hike on the flat terrain. In addition, there are both indoor and outdoor arenas, as well as trails for horseback riding, and a couple of outstanding golf courses. The Talbot County Parks & Recreation Department operates 15 community-based facilities. These facilities include sports and recreation areas for both children and adults. 

Hog Neck Golf Course, located near Easton, is a Talbot County-owned 27-hole public course that features a 7,048-yard 18-hole championship layout, and a 2,172-yard 9-hole executive course. The course has a four-star rating from Golf Digest. http://www.hogneck.com/

Harbourtowne Golf Resort & Conference Center includes a championship Pete Dye-designed course, a 50-slip transient marina, conference center and other amenities. 

The Easton Club is an 18-hole public course with full clubhouse and pro shop facilities. 


Chesapeake College in Wye Mills is a regional community college founded in 1965 and located on a 170-acre campus. Annually the college registers over 17,000 students in non-credit courses that offer opportunities to explore new cultural or educational experiences. The college enrolls nearly 4,000 students in its credit programs. 

Anne Arundel Community College in Arnold (about 27 miles) has an enrollment of about 6,500 full-time students. 

Bowie State University in Bowie (about 39 miles) has a full-time enrollment of about 3,500 students. http://www.bowiestate.edu/

Senior Programs

Talbot County Department of Social Services, Easton 

Among its many certification and non-credit offerings, Chesapeake College offers adults lifelong learning opportunities in a number of areas, including computers, crafts, outdoor interests, fitness, writing skills, and more. 

Senior Coordinated Care (Senior Care) is a coordinated system of community services for the elderly provided jointly by the local aging, social services, health and other agencies. The program is managed through a cooperative agreement between local aging, social service and health agencies. http://talbothealth.org/


Memorial Hospital at Easton is a 137-bed full service hospital with a 33-bed skilled nursing unit. 

Dorchester General Hospital in Cambridge (about 19 miles) is a 66-bed acute care facility with a full-range of inpatient and outpatient services. http://www.shorehealth.org/


Easton Airport offers two lighted runways. Charter service is available. 

Baltimore-Washington International (about 41 miles) — http://www.bwiairport.com/

Ronald Reagan Washington National (about 81 miles) 


The average temperatures for January are a low of 29 degrees and high of 44 degrees. The averages for July are a low of 68 degrees and high of 87 degrees. 


The Star Democrat (Easton’s weekly newspaper) 

Property Taxes

Assessment Office, Easton, MD (410-819-5920)

Chamber of Commerce

Talbot County Chamber of Commerce includes Easton, St. Michaels, Oxford, Tilghman Island, Trappe, and Wye Mills. http://www.talbotchamber.org/

Distances (from Easton)

Easton to St. Michaels – 10.2 miles

Grasonville – 21.5 miles

Tilghman Island – 23 miles

Oxford – 10 miles

Wye Mills – 12.7 miles

Bowie – 58 miles

Annapolis – 41 miles

Baltimore – 69 miles

Ocean City – 76 miles

Washington, DC – 70 miles

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