Walking around Annapolis is one of Connor and Jordan's favorite past times!

Annapolis is consistently ranked one of America’s most walkable towns for a good reason. This quaint, historic waterfront town has changed little since its inception in the mid-17th century. 300-year-old buildings now play host to restaurants, pubs, specialty shops, boutiques, art galleries, music venues, and so much more, all within a small area, making it easy to spend a day wandering around Annapolis.

Walking around Annapolis is always a treat, whether you’re in town for the day or making the most of a weekend by staying downtown.

The best way to spend a day walking Annapolis is to start on Main Street. The bustling business hub offers dozens of restaurant and shopping options. Starting at the top of Main Street and heading down the hill will bring you to City Dock, where you can grab a cup of coffee and relax on a bench overlooking the Annapolis Harbor as the boats cruise past.

From fine dining and wine bars to bakeries and ice cream parlors, there’s something for everyone in historic Stevensville! Have a night out filled with live entertainment at a festive local tavern, enjoy a casual meal at a pizzeria, or experience fine dining and first class hospitality in a vibrant atmosphere.

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In 1850, the town of Stevensville, was founded after the sale of farms owned by James and Charles Stevens and prospered as a major hub for steamboat travel across the Chesapeake Bay. Historic Stevensville is listed on the National Register of Historic Places. The town’s historic sites are open to the public on the 1st Saturday of the month from 12pm - 4pm from May through November. Sites include the Cray House, the Old Stevensville Post Office, the Stevensville Train Depot, the Stevensville Bank and Historic Christ Church.

One of Connor and Jordan's favorite dock bars on their drives to the Eastern Shore of MD!