View of Annapolis from Water
View of Annapolis from water

Annapolis pulsates with energy. It’s been around for more than 300 years and has been through colonial settlement, pirates, slavery, robber barons, political intrigues and more. But, mainly, the energy comes from a sense of adventure that visitors feel.

State Capitol from downtown
(Photo by Mark von Rintein)

Downtown Annapolis was the country’s first National Historic Landmark, created in 1966. Main Street is lined with historic brick buildings once used for shipping and commercial trade. Annapolis was the commercial powerhouse of the Chesapeake Bay, essentially putting other commercial centers around Chesapeake Bay out of business.

The town contains more original 18th century buildings than any other U.S. city. Five of the Georgian mansions are open to the public. Others are still used for homes or have been turned into offices, shops or restaurants. Walk any direction from the business district and you’ll find beautifully maintained Victorian and 19th Century mansions, as well as colonial watermen cottages.

Boats tied up at City Dock
(Photo by Mark von Rinteln)

Annapolis calls itself the “Sailing Capital of the World.” Actually, it competes with Newport, Rhode Island for the title. Newport has hosted America’s Cup regattas, while Annapolis leads in number of boats compared to the population. But the Annapolis city council settled it by passing a proclamation in 1995. So, there you go Newport.

The main places to see are City Dock (the waterfront),  Main Street (the business/shopping district), State Circle (state capitol area), U.S. Naval Academy, Eastport (historic neighborhood of former watermen homes), and West Street (uptown area of bars & restaurants). Then, there are a number of off-the-beaten-path areas that are fun to visit.

Annapolis Visitors Center
Annapolis Visitors Center on West Street

The Visitor’s Center (26 West Street) is a good place to start. It has public restrooms and several people standing by to answer questions. They also have maps. A particularly good one is the self-guided Historic Walking Tour. There’s also a free walking tour app so you don’t have to stop by the center. You get an abbreviated tour on your smart-phone or tablet.

Annapolis Tour Guide in Colonial Costume
Tour of Annapolis

The Visitor’s Center also has contact information for guided tours by private companies. Some are given by guides in colonial costume. The times of the tours change depending on the season, so go online or call first if you’re on a tight schedule.  A number of companies offer tours in many different modes and topics: ranging from pub crawls to food tours; ghost tours and historic home tours; kayak and boat tours; or land-based Segways. Just pick a style that fits you. Tours generally start from the Visitor’s Center or Market House near City Dock.

City Dock


Ego Alley in Annapolis, Maryland
Boats pivoting in Ego Alley, named for the boats that park along Annapolis Harbor

City Dock is the downtown waterfront harbor. It’s the city center of Annapolis and wraps around “Ego Alley,” a waterway from the harbor that dead ends in downtown Annapolis. Boats of all sorts and sizes continuously motor down “Ego Alley” to see and be seen. They “pivot” at the end of main street and go back into the main harbor. This happens continually through boating season (early spring to late fall). Sailboats, power-boat cruisers and yachts are typically tied to the Ego Alley wall throughout the year.

City Dock, at the end of Ego Alley
(Photo by Mark von Rinteln)

There’s a nice place to sit and watch the boats at the end of Main Street, but if you walk along the water, through the parking lot, you’ll find a wider park with benches that’s even better and slightly less crowded. There are a number of restaurants in that area with outside tables viewing the water (see the Eats & Drinks section).

Market House is the renovated indoor market across from City Dock with a small food court inside. It also has public restrooms and an ATM.

Annapolis Water Taxi
Annapolis Water Taxi, good for riding from Annapolis City Dock to Eastport, or from boat to shore

Next to Market House is the Kunta Kinte-Alex Haley Memorial, marking the former port of entry for slaves. Kunta Kinte, the African ancestor of author Alex Haley, arrived  on a slave ship in 1767. The memorial features life-sized bronze sculptures of Haley and three children of different ethic backgrounds. You can also catch the water taxi at City Dock. The skippers know the restaurants and will help you out.

Main Street

Downtown Annapolis, Maryland
Downtown Annapolis near City Dock & the harbor

Main Street goes from City Dock up the hill to the State Capitol. You’ll find the city’s biggest selection of boutiques, specialty shops and art galleries along Main Street, as well as a variety of restaurants. There’s a constant turn-over, so you can always return and find something new.

Here’s a list of what you’ll find.

The shops extend on side streets close to City Dock. Hobo handbags, sold around the world, started in Annapolis and the flagship store (194 Green Street) is in a renovated 19th Century townhouse just off Main Street near City Dock.

State Circle

Maryland State Capitol

Maryland State Capitol
(Photo by Mark von Rinteln)

The Maryland State Capitol is located on the top of the hill. Main Street ends at State Circle, the street going around the capitol. It’s the oldest state capitol in continuous use, topped by the largest free-standing wooden dome in the United States. The dome was constructed without nails.

The Capitol is  open to visitors 9am-5pm, daily except for Christmas and New Year’s day. Tours are self-guided, but tour companies offer a stop at the Capitol as part of their look at the city. You can find more information at the Visitor’s Center.

The entrance to the Capitol is on the side away from the waterfront, facing a promenade edged by colonial-style, brick, state office buildings. The main entrance is up the 27 granite steps. There’s a ground floor entrance under the steps. Walk around the side of the steps and you’ll see the entrance.

Maryland House of Delegates Chamber
House of Delegates Chamber

No matter which entrance you go through, be prepared to show ID to a guard and walk through a metal detector. The House and Senate chambers are on the second floor. The Governor’s office is on the ground floor.

The current House chamber, called the State House Annex, was finished in 1905 and features marble quarried from Italy and Maryland, and five Tiffany leaded glass skylights. The House Chamber seats 141 delegates, three from each of the state’s 47 districts.

The Senate Chamber is also topped by a Tiffany skylight. Forty-seven Senators fill the smaller room, sitting by party and seniority. The four committee heads sit closest to the rostrum. The state assembly meets each year for 90-days beginning the second Wednesday in January.

Maryland Governor's Mansion, "Government House"
Governor’s Mansion, called “Government House”

Much of the work of the state is done year-round on the ground floor. That’s where the Governor’s office is located, along with the Speaker, assorted staff and media rooms. You may find proposed legislation (bills) in  a rack down the hall from the shoe-shine stand, left out for the public to read. Down a side corridor, you’ll find vending machines and an ATM.

The governor’s mansion, called “Government House,” is across the street from the front of the Capitol building, behind a black wrought-iron fence. Maryland governors have been living here since 1870. It’s gone through several renovations and additions. The seven public rooms reflect those eras. Tours of Government House are given on Monday, Wednesday, and Friday, from 10:30am-12:00pm, by appointment only.

 The Circle

State House Inn, Annapolis
State House Inn has been restored a number of times. The latest addition was in 1900. The terrace was once the town well and fig garden.

State Circle (the street that encircle the state capitol) has several restaurants and historic inns or B&Bs, that cater to politicos during session and tourists when the state legislature is not meeting. There is street parking in this area, but it’s tough to come by. Watch the signs to ensure you don’t park in a reserved spot, and keep track of the time. Annapolis is strict on parking rules.

Maryland Inn, Annapolis
Maryland Inn. Delegates of the U.S. Congress stayed here when when George Washington ratified the Treaty of Paris, 1783-84.

State House Inn is one of the historic inns around the circle. It was a private home for the state’s governors and over 200+ years became a hotel and restaurant. You can see the Annapolis Harbor from some of the rooms facing down the hill.

Nearby, there’s also the city’s most recognized historic inn, Maryland Inn, and around the circle is the Governor Calvert House and Robert Johnson House.

Maryland Avenue

Maryland Avenue in Annapolis
Maryland Avenue

Several side streets shoot off State Circle like spokes of a wheel. Maryland Avenue is one of them that’s worth a visit. It’s only three-blocks long and dead-ends at the Naval Academy.

Maryland Avenue could be considered Annapolis’ antique row. On the block closest to the Capitol, antique stores, consignment and artisan shops share the street with a flower shop, tailor and laundromat. It’s a mix of ‘touristy’ and local necessities.

Artist Karin Karlsson making jewelry
Artist Karin Kalrsson makes jewelry in her shop located in the window of a West Street shop

The small business district tapers off on the second and third blocks down from the Capitol. On one side of the avenue, there’s a used bookstore which hosts author signings and other events, as well as an art gallery. The other side is a row of historic private homes. The bottom of Maryland Avenue (down the hill from the Capitol) is a couple blocks from the Annapolis waterfront. And if you continue walking, you’ll go past historic homes and manicured gardens. It’s a pleasant walk.

U.S. Naval Academy

U. S. Naval Academy at the entrance of Severna River to the Chesapeake Bay
U. S. Naval Academy at the entrance of Severna River to the Chesapeake Bay
(Photo by Mark von Rinteln)

The U.S. Naval Academy is down the hill from the state capitol where the Severn River flows into the Chesapeake Bay. The students (men & women) are midshipmen on active duty in the U.S. Navy.

When they graduate after four years with a Bachelor of Science degree, they are commissioned as Ensigns in the Navy or Second Lieutenants in the Marine Corps for at least five years, to repay the government for their education.

The “Yard,” as the campus is called, is a mix of early 20th-century and modern buildings. Newer buildings are tucked among the historic in the limited space, so there’s no quad of a typical college campus.

Macdonough Hall gymnasium at Naval Academy, Annapolis
Macdonough Hall gymnasium

Also scattered about are historic markers. Revolutionary War naval hero John Paul Jones is buried in a crypt beneath the Academy Chapel.

The campus is constant activity, weekdays and weekends. Middies dressed in fatigues can be marching in tight formation around one corner, while others in white-dress uniforms stroll nearby and another group, looking like regular college students in street clothes, practice drills and exercises on any open green-space they can find.

Naval Academy Officers' Quarters, Annapolis
Officers’ Quarters on the Naval Academy

The academy is open to the public, but access can be limited depending on what’s going on any given day.  Check security restrictions before visiting. The hours vary depending on the time of year.

To get in, anyone over the age of 16 must show a valid photo ID, then you walk through a metal detector. Tours are available at the visitors center once you get in. Visitors are restricted from many areas, and some areas will prohibit jogging, cycling and pet walking.

U.S. Naval Academy visitor's entrance
U.S. Naval Academy visitor’s entrance

The main visitors entrance is through Gate 1, a couple short blocks from the Annapolis Harbor. There is visitors parking, but only for those with a guest pass. The academy does not issue guest passes to general visitors. The average tourist must find street parking or use city parking. On event days, you can park your vehicle at the naval academy stadium and ride the courtesy shuttle (make sure one is operating first). A small bicycle rack is anchored at the entrance. It’s easiest to walk over.

St. John’s College

Entrance to St. John's College
Entrance to St. John’s College

The older  St. John’s College is nearby. It was started nearly 150 years before the Naval Academy.  Founded in 1696, St. John’s is the third oldest college in the U.S., after Harvard and William and Mary.

It’s in a neighborhood of historic wood-frame houses where an occasional brick home was mixed in. Students can be seen playing croquet on the expansive quad. The highly unusual St. John’s offers only one bachelors degree, Liberal Arts. Students are required to read the Great Books of Western Civilization.  They attend tutorials and seminars rather than formal classes. A major sport at St. John’s is croquet. Each Spring, “Johnnies” challenge Naval Middies to a match. It’s a big annual event in Annapolis.

West Street

West Street in Annapolis
West Street

The “West Street” area is the uptown of Annapolis. The district goes along West Street from Church Circle to West Gate Circle. The street is bordered by bars, restaurants and art galleries.

Church Circle contains St. Anne’s Episcopal Church, founded in 1692, and famous for its two Tiffany windows. The building is not the original. The previous building burned and was replaced with the current Romanesque Revival structure in 1858.

The church has guided tours on the first and Mondays of the month from 10am-11am and on Wednesdays from 12:30pm-2pm. The church is open to visitors daily, but walk in quietly as there may be people in reflection or prayer.

After the first block, West Street is sprinkled with banks and offices. But a number of restaurants continue for several more blocks.

First Sunday Arts Festival in Annapolis, Maryland
First Sunday Arts Festival on West Street

During the day, restaurants keep it a busy street. But at night, the bars and music step up, and the street hops with a variety of pubs catering to different age groups. (see the nightlife section)

Aside from the galleries, there’s not much shopping on West Street. But on the first Sunday of the month, from May through October, it becomes the site of the First Sunday Arts Festival. The street is closed and artisan booths line the curbs.


Historic Homes

Annapolis has more 18th Century buildings than any city in the United States. Most are private homes or businesses; only a few are open to the public. Tour availability depends on the season and the availability of volunteers. If you’re on a tight schedule, call ahead to confirm that they’ll be open and the tour schedule. The times are most solid during the summer months and less so “off-season.”

Hammond Harwood House built in 1774
Hammond Harwood House built in 1774

The Hammond-Harwood House (19 Maryland Avenue) is one of the huge merchant mansions. It was built in 1774 and stayed in the same family until sold to St. John’s College in 1926. The furniture was also sold off and St. John’s started looking for period furniture to replace it. An historic association bought the house in 1940. This means the house and its contents are still very much of the period. Only guided tours are available. They begin at the top of the hour, and the tour times vary depending on the season. There is a fee for the tour, but the garden is included. Check the website for cost and times.

William Paca House built from 1763-1765
William Paca House

The nearby William Paca House (186 Prince George Street) is what’s called a five-part Georgian mansion. The original part was built in 1763 by Paca, one of Maryland’s signers of the Declaration of Independence. The house went through several owners and at one time was a hotel. It was saved from demolition in 1965 by an historic association and is currently being renovated room-by-room as money comes in.

Hogshead, historic house in Annapolis
Hogshead, a living history house on a side street off Main Street

The house is known for its two-acre English-style Colonial garden. Guided tours of the house begin at the top of the hour; visitors can wander the garden until tour time. Check the website site for tour times and fees.

The same historic association that owns the Paca House also owns historic Hogshead (43 Pinkney Street), one of the small wood homes just off Main Street. It’s free, but open only on weekends during boating season, end of March through the Fall and during special events. Volunteers dressed in colonial costumes explain life during the 18th Century.

Chase-Lloyd House, an historic house in Annapolis
Chase-Loyd House built in 1769

The Chase Lloyd House (22 Maryland Avenue) was built in 1769 by Samuel Chase, another Maryland signer of the Declaration of Independence. Chase never lived there. He sold the house to Edward Lloyd IV, a Maryland delegate to the Continental Congress, who finished what is now considered one of the best preserved three-story Georgian townhouses from the Colonial era.

It’s a big free-standing house and not what is considered a “townhouse” today. The home was given to the Protestant Episcopal Church in 1888 and has been a home for elderly women since then. However, the house is now an historic landmark and the first floor is open to the public on weekday afternoons, from 2pm-4pm.

The James Bryce House (42 East Street) joined the public tour circuit after the state of Maryland bought the historic landmark in 2014. Before that, the International Union of Bricklayers and Allied Craftsmen owned the house and used it for offices and rented it out for special functions. The non-profit Historic Annapolis maintains and operates the 30-room Georgian mansion.

The five-part brick mansion is the largest and considered rather plain on the outside compared to the other Georgian mansions in the neighborhood, but more ornate inside. It was built in 1767 by James Brice, an aide-de-camp in General Washington’s army, Mayor of Annapolis and acting governor of Maryland in 1792.

Historic Annapolis moved its headquarters to the James Bryce House and is working on rehabbing it. The building is open weekdays 9am – 5pm. Group tours can be arranged by appointment.


Other Historic Places to Visit

The Banneker-Douglas Museum (84 Franklin Street) is a museum in the former Mount Moriah African Methodist Episcopal (AME) Church. The museum tells the story of African Americans in Annapolis beginning with Colonial times when slaves were dropped off at the Annapolis harbor to be sold.  Admission is free. It’s open 10am-4pm Tuesday-Saturday, closed Mondays and Sunday (open 1st Sunday of June, July & August).


Spa Creek Bridge to Eastport. The bridge is up to let a boat pass underneath.
Spa Creek Bridge to Eastport. The bridge is up to let a boat pass underneath.

Eastport is a rather independent part of Annapolis directly across Spa Creek from City Dock. Residents have declared themselves the “Maritime Republic of Eastport” and see themselves as the cooler, laid-back side of Annapolis.

You can easily walk over from City Dock (about a 10-minute walk across the Spa Creek bridge) or take a watertaxi from City Dock to the Maritime Museum.

Houses in the Eastport neighborhood of Annapolis, Maryland
Typical Eastport homes

The main part, about six blocks long and three blocks wide, is a ‘hood of small houses. The area is worth a walkabout to see the restored homes and occasional art gallery. No watermen are left in Eastport these days; but many boaters live there. The peninsula is bordered by marinas. It’s a working-man’s neighborhood with spots of historic attractions and local bars/restaurants. There’s no shopping/retail area.

The streets are narrow. Cars often have to wait their turn on the tight, two-way streets. Parking is limited. Park only in marked areas and never on red or yellow curbs. And watch the driveways. Some don’t immediately appear to be driveways. Some of the restaurants have small parking lots, but only for customers.

Annapolis Maritime Museum in the Eastport section of Annapolis
Annapolis Maritime Museum in Eastport

At the peninsula’s point, you’ll find the Annapolis Maritime Museum (723 Second Street).  Admission is free, but they do take donations. It’s on Back Creek, and overlooks the Severn River’s entrance into the Chesapeake Bay. In other words, a great water view. The museum is in Annapolis’ last oyster-packing house.

Annapolis Maritime Museum skipjacks
Artist Sharon Littig paints  oysterman’s boat outside the Annapolis Maritime Museum

Exhibits show how oysters were harvested and canned. There’s an interesting tidbit on the Oyster Wars from 1865 to 1960. The state is still fighting oyster poachers. The museum also has several watermen boats on display. Eastport still has several former boat-building yards. Now, they mainly repair and sell boats.

Thomas Point Shoal light station
Thomas Point Shoal Light Station in the Chesapeake Bay

From the Maritime Museum, you can catch a tour (by boat) of the Thomas Point Shoal Lighthouse 1.5 miles off shore. It’s the last screw-pile lighthouse on the Chesapeake Bay; those are lighthouses built on platforms over pilings screwed into the bottom of the bay. They look like hexagonal houses on spidery legs holding them above the water.

Davis Pub in the Eastport neighborhood of Annapolis
Davis Pub in Eastport

The area has several fine restaurants and fun neighborhood bars. Davis Pub has been featured on several food shows. The Boatyard is packed with boaters just off the water on good weather days. To find more, see the Eats & Drink section.

Several of the marinas offer short-term docking for those who want to visit the restaurants by boat. Or call the water taxi if you’re anchored out. The taxi skippers are happy to point the way for you once you get on land.

Village of West Annapolis

Village of West Annapolis
Village of West Annapolis

Off the beaten path is the Village of West Annapolis. It’s a bohemian district along Annapolis Street; two blocks of brightly painted antique stores, consignment shops and other retail, including art supply stores. It’s what could be considered the artsy district of Annapolis.

The area became part of Annapolis in 1951 and is a collection of homes built mainly in the 50s and 60s. The area is now known for having a number of salons and day spas.

The consignment and antique stores specialize in fine antiques and vintage clothing. Most, but not all, are closed on Sundays. The ones that are open have shortened Sunday hours. It’s not within walking distance of downtown Annapolis, but you’ll find plenty of free parking on the street or in the small parking lots behind the buildings.

What Else?

Okay, you’re in Annapolis and it’s raining or you’ve already seen everything, what else is there to do? The Visitor’s Bureau keeps an up-to-date events calendar. Check it out. But you can also travel farther out…

Great Frogs Winery

Great Frogs Winery
Great Frogs Winery

A couple from California started Great Frogs Winery (3218 Harness Creek Road, Annapolis, MD 21403) in 1999 with French Bordeaux varietals planted in Annapolis’ naturally sandy loam soil. They say Chesapeake breezes protect the vines from the frost and humidity dealt with inland.

This is not the typical Maryland sweet wine. It’s award winning, dry, white and red wines. A private tasting and tour is $25 per person and you have to make an appointment to stop by. It’s about three miles south of Annapolis, off of Forest Drive (Rt. 665). You’ll find a pastoral setting with an historic tobacco barn that now houses wine barrels. 

London Town and Gardens

Londontowne Pub in London Town
William Brown House

Historic London Town (839 Londontown Road, Edgewater, Maryland) is a county park on the South River in Edgewater, just outside Annapolis. But it’s not a place where you pack a picnic to play in the water. It’s the location of the William Brown House, also called the “Londontowne Publik House,” a Colonial-era tavern and farm, built between 1758 and 1764. The tavern was used for many things over the years before being taken over by the county. It’s been restored to its original state.

Colonial village in London Town
Colonial village in London Town

The farm buildings are being reconstructed based on the findings from archeological digs. It’s a small Colonial village now. Volunteers in colonial costumes are often there on weekends, doing colonial chores and explaining life during that period.  

South River from London Town pub
View of South River from William Brown House

It has a beautiful view of the South River and is rented for weddings and special occasions. The London Town Foundation also hosts a number of events through the year and runs the modern museum nearby. Check the website for admission fee and events.

World War II Memorial

The Annapolis WWII Memorial (1919 Governor Ritchie Hwy, Annapolis, MD 21409) is on the other side of the Severn River and overlooks the Naval Academy across the lovely Severn. Even if you’re not into war memorials, it’s worth a visit for the view. Just below the memorial is a little waterfront park — Jonas Green Park — with a picnic area, fishing pier and boat access to the river.

Markets & Antiques

Annapolis Amish Market
Produce section of Annapolis Amish market on Solomons Island Road

Annapolis has a popular Amish market on Solomons Island Road near the South River. The Pennsylvania Dutch Farmer’s Market (2472 Solomons Island Road) is in a strip mall next to a movie theater.

Most of the products come from Lancaster County in Pennsylvania using traditional PA Dutch recipes.

The indoor market has fresh produce, a traditional butcher’s meat counter, an amazing bakery, foods in bulk, a variety of home-made style sides for take-out and a small restaurant featuring hearty “homemade” breakfast, lunch and early dinner. There’s almost always a line for the restaurant, so give yourself time if you want to eat in.

PA Dutch Farmer's Market, Annapolis, MD
Bakery at the PA Dutch Farmer’s Market, called the “Amish Market” by locals

It’s not like a local bake-sale; the items are bulk-homemade, sold professionally packaged and presented. Customers are served by number at the super-busy meat counters, so look for the little number dispenser on the counter.

There’s also a small Amish furniture store in the back behind the bulk spices section. The PA Dutch who work there are friendly and helpful. It’s open Thursday-Saturday.


If you like antique stores, check out Annapolis Antiques (27 Riverview Avenue). You can see it off Highway 50, but it’s tricky to get to. Using a GPS is recommended. It’s an antique mall in an old building surrounded by boat storage and junk. The mall goes on and on around corners & through rooms. You can stop by the nearby Heroes Pub, known for its sandwiches and jumbo steamed shrimp with onions. The pub is named for its primary clientele, first responders.


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