Forget Boston, Retire To This Chesapeake Bay Gem With Milder Winters And Historic Streets
Boston is a standout world-class city packed to the gills with unbeatable culture, historic charm, plenty of recreational ops, fabulous dining, and A-list sports teams. Additionally, with endless greenery, striking architecture, and gorgeous water views of Boston Harbor and the Charles River, there's no denying the city's allure for active retirees. That's until you realize Boston's wicked-cold winters can drop to a bone-chilling 23 degrees on average, bringing dreams of an outdoorsy retirement to an instant halt. However, you won't have this problem further down the East Coast in picturesque Annapolis, a Chesapeake Bay gem lined with historic streets and graced with milder winters.
Annapolis is nestled where the Chesapeake Bay meets the Severn River. Established in 1649, Maryland's state capital is one of America's most historic, picturesque cities. The Maryland State House, the oldest in the country in continuous use, served as the U.S. Capital after the Revolutionary War, and Annapolis has famously been home to the U.S. Naval Academy since 1845. Its rich provenance makes for a scenic urban marvel where retirees can settle down among cobblestone streets that trace the Founding Fathers' footsteps, particularly in the National Historic Landmark District. Residents also enjoy the city's glittering maritime heritage in neighborhoods like Eastport, a boating paradise with stunning water views and bayside dining.
When winter rolls around, don't rule out hitting the trails that blanket the city's dozens of parks, or zipping about its pretty streets. For active retirees, one of the best things about living in Annapolis is that its milder winter climate makes it possible to enjoy the city year-round. Average winter temperatures fluctuate between 31 and 43 degrees — cold, but not nearly as frigid as Boston. Snowfall lasts from November through March and averages about 15 inches, considered light by national standards.
Settle down in these scenic Annapolis neighborhoods with rich colonial and maritime history
As one of "America's prettiest cities," drenched in old town, European vibes, Annapolis boasts an array of historic neighborhoods running the gamut from walkable, waterfront living to suburban sanctuary. The United States Census Bureau reports that just over 20% of residents are aged 65 and over, suggesting you probably won't be the only retiree in your new neighborhood.
For vibrant, history-rich living on the beautiful bay, look no further than the downtown Historic District, a lively cultural hub dripping in colonial, Georgian, and Federal architecture. More than 100 original 18th-century buildings line this neighborhood packed with landmarks, from the Maryland State House to the William Paca House and Garden, a Georgian mansion built for the former Maryland governor and signer of the Declaration of Independence. Walkable Main Street, a bustling thoroughfare riddled with delicious restaurants, cozy cafes, fun shops, and art galleries installed inside charming, historic buildings, is right on residents' doorsteps. Before settling down here, keep in mind that housing is subject to the city's historic preservation standards.
Across the water from downtown lies Eastport, a relaxed residential enclave in Annapolis with stunning Chesapeake views and a tasty, dockside food scene hosting Annapolis Restaurant Week. Brimming with historic bungalows and contemporary residences, Eastport is pitched on land used for encampments and forts during both the Revolutionary War and the War of 1812. Living here settles you firmly in the heart of Annapolis' maritime heritage. You can join the local Eastport Yacht Club, a hub for boating classes and events, gather with fellow residents to watch the club's weekly summer sailing races, and take part in the happenings at the neighborhood's award-winning Annapolis Maritime Museum & Park.
Get active in the community and revel outdoors during Annapolis' mild winters
The community geared toward retirees in Annapolis revolves around various clubs and organizations focused on art, culture, and maritime activities. Joining the Annapolis Yacht Club, volunteering with the preservation nonprofit Historic Annapolis or the dynamic Maryland Hall arts center, and attending events at the Annapolis Senior Activity Center – which organizes classes, games, and a robust roster of affordable day trips – are top places for transplant socialization.
Annapolis' climate means it's possible for residents to enjoy being outside and staying active all year. In fact, December transforms the streets of Annapolis into a winter wonderland that beckons residents outside with a host of traditions. The Annapolis Holiday Market, the Eastport Yacht Club Lights Parade, and the late-night, entertainment-filled holiday shopping event "Midnight Madness" lure bundled-up residents out of the house. Among the city's dozens of pretty parks, Quiet Waters Park leads the pack for wintertime recreation. This 340-acre forested sprawl is dappled with sculptures, a network of paved trails, and the ultimate in winter fun: a seasonal, outdoor ice rink. The winter season also yields some solid birdwatching for the park's waterfowl, with roughly 20 species fluttering about. Keep your eyes peeled for Common Loons, Swamp Sparrows, and Winter Wrens, along with a variety of songbirds and ducks.
Outside of walkable neighborhoods, having a car makes getting around Annapolis convenient, especially if the city's buses, shuttles, water taxis, and car taxis aren't easy to access in your neighborhood. Annapolis is located roughly 40 minutes from both Baltimore, where you won't want to miss these nine secret spots, and Washington D.C., another retirement hub filled with events and attractions. There is one main hospital in Annapolis, Luminis Health Anne Arundel Medical Center. Additionally, note that all of these retirement perks come at a cost of living that's 27% higher than the national average.