This Chesapeake Bay Downtown Is the Most Walkable

Annapolis is one of the most uniquely laid-out towns in the Chesapeake Bay area, and one of the most walkable. State Circle and Church Circle are home to some of the state's most historic landmarks, including the Maryland State House and St. Anne's Episcopal Church. Shops like Evergreen Antiques on Maryland Avenue and restaurants such as O'Brien's Oyster Bar & Seafood Grill along Main Street provide hours of entertainment. When it's time to rest after a day spent exploring downtown Annapolis, lodging is conveniently available downtown at the Flag House Inn on Randall Street or the 86 State Circle Luxury Boutique Hotel. So, come explore this historic town's thriving downtown area on your next vacation to Maryland.

Historic Downtown Annapolis

The seaport town of Annapolis was named after Princess Anne, heir to the British throne, in 1708. The Annapolis flag displays Princess Anne's royal badge, a crown over the interwoven thistle of Scotland and Tudor rose of England. Designed by Royal Governor Sir Francis Nicholson, Annapolis' unique downtown was created with circles with radiating streets, similar to the baroque design of some of Europe's capital cities. One circle contained St. Anne's Episcopal Church, while another contained the State House.

Annapolis was a bustling shipping town, and its merchants and businessmen built mansions with formal ballrooms and gardens in the 18th century. Today, more of these original structures are standing in Annapolis than in any other U.S. city. Many, such as the William Paca House and Garden, a Georgian mansion built by a signer of the Declaration of Independence, can be visited in Annapolis' downtown area today. It is located on St. George Street and is within easy walking distance to the Maryland State House at 100 State Circle, the nation's oldest state house in continuous legislative use. Visitors can tour the State House, which was used as the U.S. Capitol from November 1783 to August 1784. From the State House, a short walk down Maryland Avenue will take you to the U.S. Naval Academy Museum. It is open to the public for tours, as long as you show two forms of identification upon entrance.

Downtown Annapolis Shops and Eateries

Heading back up Maryland Avenue, you will encounter specialty shops and eclectic eateries along red brick-lined streets. Check out Galway Bay Irish Restaurant and Pub for authentic Irish-inspired food and drink. Local By Design, just a few stops down Maryland Avenue, showcases art, jewelry, furniture, home decor, and more created by local artisans.

Walking back towards State Circle, you'll find The Annapolis Pottery, a shop specializing in handmade goods, ceramics, and home decor. Take a walk around the circle in a counter-clockwise direction and you'll come to Annapolis Ice Cream Company on Main Street, the only store in Historic Annapolis with ice cream made on site daily. The Cottage on Main, also on Main Street, sells women's clothing, jewelry, and accessories, as well as children's clothing and wellness products.

Walking Tours And Outdoor Activities In Annapolis

If you prefer a guided walking tour of downtown Annapolis, book a tour with Watermark Walking Tours, which meets on Main Street near Annapolis Ice Cream Company. Private, group, and specialty tours are available. Specialty tours focus on themes such as "Scandalous Annapolis," guided by a character dressed in period costume as a servant who knows all about her rich bosses' escapades.

As Annapolis is a port city, many opt to take a water cruise to see the downtown area instead. Head down Main Street towards the water to Compromise Street just across from the City Dock, and you'll find Schooner Woodwind Annapolis Sailing Cruises. From April through November, you can take a sail on a 74-foot schooner in the Chesapeake Bay and see the beauty of downtown Annapolis from the water. Public and private cruises are available.

Accommodations In Downtown Annapolis

Conveniently located where Annapolis Sailing Cruises board is the Annapolis Waterfront Hotel, across from the City Dock. Rooms with bay views, views of the historic downtown area, and private balconies are all available. A fitness center and restaurant are also on site. If a bed-and-breakfast is closer to your idea of comfort, you can head back up Main Street to the Inn on Main. This hotel, right in the downtown area, has 10 spacious rooms and is intended to make visitors "feel like locals."

For a truly historic lodging experience, check out The Maryland Inn on Church Circle, where Main Street meets Church Circle, just across the street from the Maryland State House. The hotel features 18th-century architecture and luxurious rooms, including free Wi-Fi. A 24-hour fitness center and Drummers Lot Pub are also on site.

Other Chesapeake Bay Walkable Downtowns

With its circle design, as opposed to a traditional grid design, Annapolis' downtown area truly stands out. There are other notable downtowns in the Chesapeake Bay area, however, that share its history, colonial-era architecture, harbor-focused commerce, and style. Chestertown is one such downtown. About 50 miles from Annapolis, Chestertown's historic area includes 18th-century homes, historic landmarks, shops, and restaurants. Be sure to check out the Custom House on Water Street, part of Washington College and a riverfront landmark for three centuries. Grab a bite to eat and a drink at the Kitchen & Pub at the Imperial at Garfield Center, just up High Street from the waterfront. It is known for its farm-to-table, casual fine dining excellence.

Another historic, walkable downtown similar to that of Annapolis is St. Michaels. Also, 50 miles from Annapolis, St. Michaels is a classic, walkable waterfront town with a deep-rooted maritime history, just like Annapolis. Don't miss the Chesapeake Bay Maritime Museum along the harbor on Talbot Street, where you can learn more about the rich history of the area. Also on Talbot Street is The Fool's Lantern Wine & Taproom, serving casual food, drinks, and entertainment.

Visit Strollable Annapolis

Annapolis, Maryland, is often referred to as the "Athens of America" because, like Athens, it has long served as a center of culture and a sophisticated social life in the country. Today, Annapolis' well-preserved rich history draws over 4 million people to this Chesapeake Bay town each year. Downtown Annapolis is easily explored on foot, and its walkable streets feature both historical and modern attractions that cater to every kind of traveller. Although it is the capital of Maryland, Annapolis has a relatively small population of around 40,000 residents, allowing tourists to enjoy its small-town charm and the many welcoming local businesses in the downtown area.