Annapolis, Maryland

Best Places to Retire in Maryland


Annapolis (population 35,000) is among the oldest cities in the U.S., dating to 1649. Located on the western shore of the Chesapeake Bay at the mouth of the Severn River, it is conveniently near two major cities: Washington, D.C., 35 miles to the southwest and Baltimore, 27 miles northeast. It is the Maryland state capital and is called the “Sailing Capital of America.” It is known as the home of the United States Naval Academy. The earliest settlers found American Indians building log dugout canoes for fishing and moving about the Chesapeake Bay, and boat building became one of the first industries. Like all other port communities, Annapolis was long dependent upon waterborne transportation for nearly all its necessities. Annapolis was made the capital of Maryland by its royal governor, generations before the American Revolution. Queen Anne chartered her namesake as a city in 1708. The Treaty of Paris ending the Revolutionary War was signed in Annapolis. The homes of the four Maryland signers of the Declaration of Independence are still standing in the city. The structures and institutions like the State House, the historic City Dock and the many Georgian-style homes in the historic district provide links to its past. African-Americans have been a part of the community since its earliest days and their experience from slavery days, the Civil War and the Civil Rights movement are preserved in monuments, homes, churches and museums. During the 19th century, African-Americans comprised one-third of the population in Annapolis.

Annapolis and sailing have been seen as nearly synonymous over the centuries. It has been, and is today, a popular port-of-call for ocean going yachts. It is perhaps only fitting that the largest in-water boat shows in the world are held here each October — the United States Sailboat Show, followed by the United States Powerboat Show. The Chesapeake Bay is also well-known for fishing, recreational boating, and its watermen who earn their living from its harvest. Maritime activities are a big part of the economy of the region.

The Naval Academy was founded in 1845 with seven professors and 50 midshipmen. Today, the Academy has expanded to 338 acres and enrolls 4,000 midshipmen (both men and women). It offers a core curriculum plus 18 major fields of study, advanced studies, and research opportunities.

Barron’s magazine selected Annapolis as one of the top 10 places to retire. Among the reasons cited was the wide range of activities, classes, the arts, history, its proximity to recreational and educational resources, and easy access to major metropolitan areas. You can add to this list the wide choices in dining – anything from fast food to pubs, great casual seafood restaurants, and fine Italian or American dining. And within little more than an hour, you can be at the John F. Kennedy Center for the Performing Arts, the National Air and Space Museum, or the Smithsonian Institute. Or, you could be up in Baltimore at the National Aquarium or at an Orioles baseball game.

Arts & Culture

Annapolis Summer Garden Theatre offers outdoor performances for 15 weeks during the summer months.

Annapolis Opera has five performances in the spring and in late fall. Performances are held at the Maryland Hall for Arts.

Annapolis Symphony Orchestra has performed for more than 40 seasons. It performs a five-concert Classic Series, a Family Series, a Holiday Pops concert and at special events.

Ballet Theater of Maryland is a professional dance company offering ballet productions, lectures, demonstration and dance instructions. Most performances are at the Maryland Hall for Arts.

The Annapolis Chorale offers a full fall and spring performance schedule.

Chesapeake Arts Center is a major venue in Brooklyn Park, MD with a 904-seat, state-of-the-art main stage theater, a 110-seat studio theater, a dance studio, a clay studio, a woodshop, classrooms and studio space.

Chesapeake Music Hall is a premiere dinner theatre featuring a buffet and quality Broadway-style shows on Fridays, Saturdays, Sunday matinees, and selected weekday performances.

Maryland Hall for the Creative Arts hosts chorale, opera, symphony orchestra and ballet theatre. It also offers quality education in the performing and visual arts.

Annapolis Maritime Museum presents the many facets of the 400-year story of Annapolis; the history of men and women living and working in and around this port city.

There are a number of fine galleries – too many to list here. What follows are just a few — with their Web links.

McBride Gallery has seven rooms of original paintings, sculpture and fine graphics.

Mitchell Art Gallery, at St. John’s College, has museum quality exhibitions and offers talks, tours and children’s programs.

Nancy Hammond Editions offers limited edition silkscreen prints.

ARTFX offers pottery, glass, sculpture, paintings and fibers featuring local, regional and international artists.

Gallery on the Circle, operated by the Maryland Federation of Art — a non-profit arts organization — features local and regional artists in all media.


Boat shows are “great recreation” for boaters! The two largest in-water boat shows in the world are held each October in Annapolis: The United States Sailboat Show, followed by the United States Powerboat Show.

Anne Arundel County Recreation and Parks Department operates 75 park facilities throughout the county. They offer a wide variety of recreation and sports activities for individuals, families, and groups. These include picnic pavilions, fresh and saltwater fishing, biking-hiking-jogging trails, birding, swimming pools, tennis courts, an ice rink, athletic fields and more.

The county owns two great golf courses, both managed by Billy Casper Golf Management.

The Dwight D. Eisenhower Golf Course is an 18-hole layout in Crownsville, MD.

The other is Compass Pointe Golf Course, which offers 36 holes stretched across more than 800 acres, featuring a beautiful, natural setting.

Sandy Point State Park is a 786-acre park on the Chesapeake Bay. It offers swimming, fishing, crabbing, boating and windsurfing. Wildlife viewing and bird watching are also favorite pastimes for visitors.

Patapsco Valley State Park extends 32 miles along the Patapsco River and encompasses 14,000 acres with five recreational areas. It offers hiking, fishing, camping, canoeing, horseback and mountain bike trails, as well as picnicking at the many pavilions.


St. John’s College is a four-year liberal arts college founded in 1696 – pre-dated only by Harvard University and William and Mary. St. John’s tries to maintain a student enrollment of approximately 450 students at each of its two campuses: Annapolis and in Santa Fe, New Mexico. The 36-acre Annapolis campus is in the heart of the city. The 250-acre Santa Fe campus is in a beautiful, natural setting.

The United States Naval Academy enrolls 1,200 midshipmen from all 50 states each summer. The Academy offers a core curriculum plus 18 major fields of study.

Senior Programs

The Annapolis Senior Center, near the historic district, offers a wide variety of activities, including art, crafts, physical fitness, dance, sewing, bridge and more.

The Capital-Gazette newspaper offers “Senior Highlights” and a calendar of Senior Center events.

Senior Services –

There are seven Senior Centers throughout Anne Arundel County.

For more information on Anne Arundel County’s Senior Centers go to


Anne Arundel Medical Center is a full-service acute care facility licensed for 248 beds. It has more than 2,000 full-time and part-time employees and over 600 medical staff members.


Baltimore-Washington International Airport –


The weather in Annapolis is decidedly influence by its location, directly on Chesapeake Bay. Summer days can be hot and humid, yet there is often and afternoon breeze off the water. The first frost is typically November 1, and last one is April 7. When there is snow, it typically doesn’t last very long on the ground.


Capital-Gazette –

Property Taxes

Annapolis is in Anne Arundel County –

State Taxes

Chamber of Commerce

Maryland Department of Aging


Baltimore, MD – 27 miles
St. Michaels, MD (Eastern Shore) – 51 miles
Washington, DC – 35 miles
Rockville, MD – 42 miles
Reston, VA – 56 miles
Philadelphia, PA – 126 miles
Gettysburg, PA – 82 miles

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