Annapolis, Maryland - Best Things To Do

Best Things To Do in Annapolis, Maryland

I grew up near Annapolis and would often hang out on Main Street and along the docks. We have been back in Maryland a lot over the past few years (check out my steamed crab recommendations), so I have been keeping notes on my favorite things to do in the state’s capital. This area is full of history and, of course, it’s a great entree to the Chesapeake Bay.

Best Things To Do In Annapolis, Maryland

Photo by M01229 on Flickr


List of Over 20 Fun Things To Do In Annapolis, MD


Baltimore & Annapolis Trail

Anne Arundel County
This 13.3-mile trail starts in Arnold and ends near the Baltimore Light Rail Cromwell Station in Glen Burnie. Built on a former rail line through the suburban region between Annapolis and Baltimore, the path winds through parks, neighborhoods and natural wooded areas providing scenic views of trees, streams and many historical points.

Baltimore-Annapolis Trail | Best Things To Do in Annapolis, Maryland

Photo by Dion Hinchcliffe on Flickr


Banneker-Douglass Museum

84 Franklin Street, Annapolis
This museum, dedicated to preserving Maryland’s African American heritage, is named for Benjamin Banneker and Frederick Douglass. The contributions of famous African American residents from Maryland are highlighted, including Benjamin Banneker, James Pennington, Frederick Douglass, Harriet Tubman, Matthew Henson, and Thurgood Marshall.

Banneker-Douglass Museum | Best Things To Do in Annapolis, Maryland


Bar Crawl

Various Locations, Annapolis
Not surprisingly, the downtown Annapolis area has a lot of bars. Most have a historical feel to them, but all have something good to drink. Start on West Street Arts district and work your way down Main Street to the city dock, or if you like a challenge … crawl uphill!

Annapolis Bar Crawl | Best Things To Do in Annapolis, Maryland


Chick & Ruth’s Deli

165 Main Street, Annapolis
While this Annapolis mainstay was sold by the original owners in 2017, the bright orange greasy spoon is still a must-stop on Main Street. It’s affordable, kitchy, fun and a great place to get comfort food in Naptown. Also, many sandwiches are named in honor of local celebrities and politicians.

Chick & Ruth's | Best Things To Do in Annapolis, Maryland


City Docks (Ego Alley)

Dock Street and surrounding area, Annapolis
The dock area in Annapolis is sometimes called “Ego Alley” because of the parade of expensive boats, either coming in and out or parked there on display. Either way, it’s a lovely place to walk around and see the boats, have some food, and/or strike up a conversation with someone who can tell you all about the waterways of Maryland.

Ego Alley | Best Things To Do in Annapolis, Maryland

Photo by Christopher Connell on Flickr


Eat Crabs

Various Locations, Annapolis
As I mentioned, I wrote a huge post of places to get crabs around Maryland, but if we are talking specifically Annapolis, I will usually choose Cantler’s or The Point. But given its close access to the water, you really can’t go wrong anywhere in the area!

Have Crabs | Best Things To Do in Annapolis, Maryland


First Sunday Arts Festival

Calvert and West Streets, Annapolis
There is a great arts district from Church Circle to Westgate Circle, so you can walk around and check out the galleries just on any regular day. But over 130 artisans come out on the first Sunday of every month in the summer to share their talents.

First Friday Art Festival | Best Things To Do in Annapolis, Maryland


Get Ice Cream – or Fudge?

Various Locations, Annapolis
All around the downtown area, there are several delicious ice cream shops. It’s pretty much a right of passage to walk around with ice cream dripping down your hand on a hot, humid day. However, there are also some places with great fudge – so hopefully all the walking allows you to have both!

Ice Cream | Best Things To Do in Annapolis, Maryland

Photo by M01229 on Flickr


Kinder Farm Park

1001 Kinder Farm Park Road, Millersville
This working farm is close to where I grew up (and close to my heart) – it’s about 30 minutes north of downtown Annapolis. The park itself is huge, encompassing over 288 acres, with trails and a large playground for family-friendly fun. The farm shows past and present agricultural practices and cares for many animals, including chickens, turkeys, geese, cows, pigs, goats, sheep, quail and alpacas.

Kinder Farm Park | Best Things To Do in Annapolis, Maryland


Main Street

Main Street, Annapolis
If you only have time for one thing, give yourself an hour or two to walk up and down Main Street and then on down to the docks. It’s the hub of downtown Annapolis and gives you a sense of the architecture – plus it’s a great spot to pick up a souvenir.

Main Street | Best Things To Do in Annapolis, Maryland


Maryland State House

100 State Circle, Annapolis
The Maryland State House is the oldest U.S. state capitol in continuous legislative use, dating back to 1772. The capitol also has the largest wooden dome in the United States constructed without nails. The State House is open to the public every day (except Christmas and New Years Day) and self-guided tour information is available in the Office of Interpretation on the first floor.

Maryland State House | Best Things To Do in Annapolis, Maryland


Naval Academy Tour & Blue Angels

52 King George Street, Annapolis
Growing up near Annapolis, I didn’t quite get what a big deal the Naval Academy was. If you didn’t know (like me), it is the second oldest of the United States’ five service academies, and educates officers for the Navy and Marine Corps. It’s also a beautiful campus that allows for public tours. Bonus, the famed Blue Angels perform at Commissioning Week every year – which you can watch from various points around town.

Naval Academy & Blue Angels | Best Things To Do in Annapolis, Maryland


Quiet Waters Park

600 Quiet Waters Park Road, Annapolis
Quiet Waters Park is situated between the South River and Harness Creek. Visitors can enjoy trails winding through forests and past grassy fields, children’s playground, or picnic among 340 acres of beautiful park land.

Quiet Waters Park | Best Things To Do in Annapolis, Maryland

Photo by Angela Smith


Rams Head on Stage

33 West Street, Annapolis
You knew I would include a music venue, right? I have seen several shows at Rams Head Annapolis, and it’s a great space. Large enough to have cool acts coming though, small enough to still feel intimate.

Rams Head Live | Best Things To Do in Annapolis, Maryland


Renaissance Festival

1821 Crownsville Road, Annapolis
Set in a fictional 16th-century English village named Revel Grove, the Maryland Renaissance Festival is spread over 27 acres in Crownsville. It’s the one of largest renaissance fairs in the United States (Texas is number one), and starts on the last weekend of August for nine weeks. Jousting is actually Maryland’s state sport, but there is much more to see at the “Renn Fest” – including art, food, stage performances and just the feeling that you have stepped back in time.

Renaissance Festival Maryland | Best Things To Do in Annapolis, Maryland


Sailing Cruise

Various Locations, Annapolis
This one seems pretty obvious, right? If you look at a map, you’ll see that Annapolis is situated on the Chesapeake Bay as well as near the mouths of the Severn, Magothy, and South Rivers. My father was a sailor, so I grew up on a boat, and I highly recommend the experience!

Sailing Cruise | Best Things To Do in Annapolis, Maryland


Sandy Point State Park

1100 East College Parkway, Annapolis
Sandy Point State Park is a public recreation area located at the western end of the Chesapeake Bay Bridge. If you don’t have time to get over to Ocean City, Sandy Point has a nice beach to relax on the sand with great views of the Bay Bridge.

Sandy Point State Park | Best Things To Do in Annapolis, Maryland


Thomas Point Shoal Lighthouse & Park

3890 Thomas Point Road, Annapolis
This a historic lighthouse is by far the most recognized lighthouse in Maryland. It is the only screw-pile lighthouse in the bay which stands at its original site. It is open to the public only a few months out of the year, so be sure to check dates before you head out.

Thomas Point Shoal Lighthouse | Best Things To Do in Annapolis, Maryland

Photo by Harry Fahl


Walking, Water or Trolley Tour

Various Locations, Annapolis
We are huge fans of doing a tour of some sort when we visit a new city, and luckily Annapolis has several kinds to offer. You can look for walking tours, go by boat, or take a trolley. The city’s population is about 40,000 people, so the tours don’t take a long time, but are a great way to get oriented.

Walking, Water or Trolley Tour | Best Things To Do in Annapolis, Maryland


Wednesday Night Sailing Races

2 Compromise Street or Spa Creek Drawbridge, Annapolis
Every Wednesday night from April through September, there is an Annapolis Yacht Club (AYC) Race. Fans can line up on near the AYC to see the start, or at Spa Creek Drawbridge to see the boats come across the finish line. Wednesday Night Racing has been a time-honored tradition in Annapolis for nearly six decades!

Wednesday Night Sailing Races | Best Things To Do in Annapolis, Maryland


William Paca House & Garden

186 Prince George Street, Annapolis
William Paca was a signatory of the Declaration of Independence and a three-term Governor of Maryland. Paca largely designed the house himself, and the 2-acre walled garden (which includes a two-story summer house) has been restored to its original state. You can go on guided tours or explore the Paca House & Garden on your own.

William Paca House & Garden | Best Things To Do in Annapolis, Maryland


World War II Memorial & Overlook

1920 Governor Ritchie Highway, Annapolis
Dedicated in 1998, the World War II Memorial honors Maryland citizens who gave their lives during World War II. In addition to being a very humbling memorial, the location is a wonderful spot to stop on the way into Annapolis for a scenic overlook of the Severn River and the Naval Academy.

WWII Memorial & Overlook | Best Things To Do in Annapolis, Maryland


There you go. Hope this list of fun things to do in Annapolis helps you plan your visit!

Annapolis, Maryland - Best Things To Do - Over 20 Fun Things To Do in Annapolis #Travel #Annapolis #Maryland

This article has 1 comment

  1. Christina

    This is a great list Aimee, thanks for sharing it!

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