Visit Annapolis MD in Fall

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Relax at a tavern visited by George Washington. Tour the state capitol where U.S. independence was born.

Annapolis, MD, is a historic charmer that’s Navy-proud and minutes from Washington, DC.

America’s freedom from its European parents was won on battlefields across the country, but on Jan. 14, 1784, that separation became official in Annapolis, MD. Inside the Maryland State House, the Treaty of Paris, negotiated between Great Britain and the United States, was ratified by the Continental Congress. The document ended the Revolutionary War and recognized the United States as an independent nation. For a short time in history — from 1783 to 1784 — that building served as the Capitol of the nascent country.

On a stroll along Annapolis’ redbrick streets, once the traffic is blotted out, it’s easy to envision merchants hurrying to shops and ladies perched in horse-drawn carriages. Annapolis, which is often called “a museum without walls,” contains a large concentration of 18th-century buildings. Its Colonial district is listed as a National Historic Landmark.

Annapolis’ historic allure and downtown walkability, a function of its 18th-century heart, appeal to retirees like Ellen Penndorf, a former dental hygienist from Fairfax County, VA. “The atmosphere is upbeat and casual. And in Annapolis you get a nice variety of people with many different interests,” she says. She has become active in a local sailing club. “I began to sail to get back into life after my husband died. I moved to Annapolis to reinvent myself,” says Ellen, who is in her mid-60s. “Sailing is a fun way to meet new people.”

Home to the U.S. Naval Academy, established in 1845, Annapolis is on the Severn River where it flows into the Chesapeake Bay, one of North America’s largest estuaries. The classic Annapolis photo depicts sleek yachts and the tall masts of sailing vessels moored at the City Dock marina — aka Ego Alley for the show-worthy crafts — against the background to 18th-century buildings.

Other water lovers are Jan and Peter O’Brien, who purchased an Annapolis condo as a second home in 2007. “I like being on the water and also watching the boats and the kayakers,” says Jan, 59. “The water is relaxing and we do a lot more things outdoors in Annapolis.”

That realization prompted the O’Briens to modify their pre-retirement strategy, relocating from Reston, VA, sooner than planned. They moved here in 2009 after their daughter graduated from high school.

“Every time we came out on weekends my stress level would fade away,” says Peter, 58, and executive with Marriott. “We decided to move for a lifestyle change. We did a major downsizing and moved to the condo full time. We love it and have never looked back.”

After morphing into Annapolitans, the O’Briens purchased a Boston Whaler. “It allows us to get around the bay,” Jan says. “Being on the water, overlooking the water is part of the overall atmosphere of Annapolis. We zip over to Cantler’s for crabs.”

Just one of the city’s famed restaurants, Cantler’s Riverside Inn has been dishing up fresh seafood for 40 years. Platters of steamed crab, the house specialty, as well as tasty crabcakes, buckets of mussels and peel-and-eat shrimp keep diners coming. At the 11 a.m. opening time, the line for a spot inside or at a picnic table on the covered deck typically snakes into the parking lot.

The Chesapeake’s bounty has lured people for centuries. Long before European settlers arrived, Native Americans fished the region’s shores for oyster and crab. As early as 1649, colonists from Virginia established the hamlet of Providence on the bay. In the mid-1690s, Maryland Gov. Francis Nicholson moved the colony’s capital north to its current site from St. Mary’s City and renamed the town Annapolis in honor of Princess Anne, who became England’s queen in 1702.

Envisioning a future, grand Annapolis, Nicholson designed the streets so they radiate out like spokes from two circles — one for the Episcopal church and the other for the capitol.

Construction of the Maryland State House, the third capitol building on that site, started in 1772. Lawmakers first met there a few years later. It reigns as the oldest state capitol in continuous legislative use.

For much of the 18th century until the Revolutionary War ended — when Baltimore eclipsed the city as a shipping harbor — Annapolis functioned as a busy customs port and the cultural center of Maryland. Ships brought iron and wooden products from New England, and rum, sugar and coffee from the West Indies. Wealthy Annapolitans built grand homes, several now open to the public. Ogle Hall, a mansion built sometime between 1739 and 1742, currently serves as the U.S. Naval Academy Alumni House.

Another grande dame, the Hammond-Harwood House, built in 1774, contains Colonial items and a collection of painting by Charles Willson Peale, noted for his portraits of Revolutionary War leaders. The Charles Carroll House, birthplace and residence of the only Catholic to sign the Declaration of Independence, dates to the 1720s.

Walk to Church Circle to find Reynolds Tavern, constructed in the mid-1700s. Merchants, soldiers and farmers imbibed at this pub, now known for its afternoon tea of scones, sandwiches and sweets. It also offers meals and lodging. The Middleton Tavern, near the City Dock on Market Space, first served as a watering hole in the 1750s. The pub and restaurant lists George Washington and Thomas Jefferson as past patrons.

In addition to rum from the West Indies, ships brought slaves from the islands as well as from Africa. Plaques lining City Dock quote passages from Alex Haley’s epic work “Roots.” In the book, Kunta Kinte, the protagonist and reportedly Haley’s ancestor, came to the New World in chains in 1767 aboard the Lord Ligonier. The Kunta Kinte-Alex Haley Memorial includes a bronze sculpture of the Pulitzer Prize-winning author reading to three children.

“Annapolis” has great appeal,” Peter says. “The history, the influence of the Naval Academy and the fact that it’s a college town contribute to the appeal. Annapolis is the state capital, so it’s very exciting in that respect.”

Home prices vary in Annapolis, says Jan, who had no intention of working after moving here until a friend in real estate suggested she might like that business. “Waterfront living comes in all price ranges,” says Jan, now a full-time agent. “You can find a small fixer-upper cottage in the Chesapeake vicinity in Anne Arundel County from $300,000 to large homes on the water in Eastport for $5 million.”

Terry and Frank Martini, both 61, purchased a townhouse in Chesapeake Harbour, a waterfront community, after relocating from Chappaqua, NY, in 2011. “I have views of the Chesapeake Bay on one side and the marina on the other,” Terry says.

A former employee at the Chappaqua library, she now works 20 to 25 hours a month as a Web developer and Frank continues as a full-time information systems consultant. Annapolis is convenient to three airports — one in Baltimore and two in Washington, DC. “Frank telecommutes and travel to client sites, so that access is important,” Terry says.

Annapolis has plenty of cultural and recreational activities. Norma Farrell, past president of New Annapolitans, a group of mostly women that welcomes newcomers, says, “I’ve heard it said that Annapolis is a camp for adults. There’s lots of boating, but we also have local theater, local arts — ballet and the symphony. And a number of sporting activities that include Naval Academy football games and baseball.”

Terry says the group is a great way to meet new people.

“I’m involved in the book clubs, needlework and gadabouts — we go on trips to DC and Baltimore,” she says.

Ellen, also a member, attends the Annapolis Symphony Orchestra, lunches with friends and goes to the Annapolis Senior Center. “I’m there two to three times a week and take classes in Pilates, aerobics, line dancing, tai chi. And I just finished a year of French and a year of wine education. These are serious classes offered by Anne Arundel Community College. What a life! I am enjoying myself,” she says.

For the theater lovers, the Annapolis Summer Garden Theatre and Colonial Players put on plays and musicals.

Two more happy Annapolis retirees are Mike Dauth, 68, a former engineer and program manager with an Air Force background, and wife Pam, 52, from Miami, who worked as a public relations executive. Mike lived in the DC area before purchasing a historic house in Annapolis in 2002. Pam and Mike, who married in 2005, retired in 2012 and 2013 respectively.

“The ability to park your car on Friday night and do almost anything you want — go to restaurants, theaters — without having to move your car is a big plus for us,” Mike says. “Our lifestyle is to be out among people, doing activities, living where we can walk to things. We wouldn’t be in a suburb or a secluded area where we had to drive to go to a restaurant or to the movies.”

Terry enjoys Annapolis’ manageable size plus the amenities in Baltimore and Washington, DC. “I like a small-town feel, but wanted to be near the culture offered in a big city,” she says.

And what about taxes? Ellen, from northern Virginia, said her taxes stayed about the same. “There was no real benefit. Taxes are fairly high and I accept that. I want good roads,” she says. But the Martinis reap a bonus. “Taxes are relative,” Terry says. “People moving from the South might find the taxes higher, but coming from Chappaqua, our taxes in Annapolis are half what they were in New York.”

Annapolis also is prone to flooding; it was ranked No. 17 of cities in the United States for nuisance flooding in a June report from the National Oceanic and Atmospheric Administration.

And Annapolis suffers through snowy, frigid winters. Last year, the Dauths purchased a winter home in Delray Beach, FL. “Most of my family is there,” Pam says. “For us, Florida has to do with family and being away from the winter cold.”

But the chilly months don’t overshadow Annapolis’ benefits, may retirees say. “We have open spaces, parks and golf courses,” Ellen says. “Access to DC and Baltimore is easy and Annapolis is a good choice for people who don’t want to be too far from their children in Virginia, DC and other parts of Maryland. I think that Annapolis is an up-and-coming place for retirees. I really like it here.”