A Day in Annapolis

Summertime means day tripping, sun soaking and memory making.  Years had passed when I began to reminisce about visits to Annapolis with friends.  The time was long overdue to bring my own family bayside.  Annapolis is home to the U.S. Naval Academy.  It’s the norm to see officers dressed in their navy whites meander through this seaside town.   I’ll highlight some of the family-friendly places in Annapolis that are worth checking out.

U.S. Naval Academy & Museum
121 Blake Rd.
Annapolis, MD 21402

If you’re fascinated with Beaux Arts architecture or want to discover where future officers are trained, step into The Armel-Leftwich Visitor Center of the United States Naval Academy.  If your children are interested in a future as a midshipman, there are a couple of opportunities.  Children ages 13 to 15 can enroll in the USNA Junior Leadership Program.  Rising high school seniors can participate in a week-long summer seminar with the USNA.  A guided walking tour to view the museum and grounds is $36 for a family, $11 per adult, $9 for military and per child in 1st to 12th grades and military and free for children below 1st grade.  If the one mile walk is too tedious, a one hour riding tour is $30 per person with a max of 5 people per vehicle.  All adults will need ID to enter the grounds.  If you are military or DOD, you and your family can drive on to the grounds.  Everyone else needs to park outside the academy and walk through Gate 1.

US Naval Academy

Maryland State House
91 State Circle
Annapolis, MD 21401

The Maryland State House is a prominent building that greets you as you enter the historic area of Annapolis.  It’s quite a fascinating structure being that it’s the largest wooden dome built in the U.S. without the use of nails.  The State House is the oldest state capitol still in use today.  On any given day, you may see the Maryland General Assembly gathering or see elected officials as their offices are here.  Take a self-guided tour from 9 a.m. to 5 p.m. daily by picking up a pamphlet from the Office of Interpretation.

Maryland State House

William Paca House and Garden
186 Prince George St.
Annapolis, MD 21401

If you’re a history buff, step inside the 18th century Georgian mansion built by William Paca.  Paca was a signer of the Declaration of Independence and Maryland’s third governor.  Guided tours of the home and self-guided tour of the two-acre garden range from $5 to $10 depending which tours you want to view.  The spring and summer are the best times to see the rose garden boxwoods and aptly named summer house.  Open daily, the William Paca House and Garden is closed in January and February.

Ego Alley
The hub of Annapolis is at the City Dock better known as Ego Alley.  Its moniker doesn’t refer to a commonly known alley, but from the steady stream of fancy sailboats and yachts.  Sit along the seawall with ice cream cone in hand, feed the ducks, people watch and take in the salty air.

Pirate Adventures on the Chesapeake

Ahoy mateys!  Board the Sea Gypsy pirate ship on the Chesapeake Bay.  Your adventure begins with a moustache or mermaid painted face and pirate attire to fully embrace the culture.  With your crew on board, fire water cannons at scallywags as you search for pirate booty.  Tours last 1 ½ hours and there is no restroom on board the ship.  While it’s a family experience including music, dancing and laughs, ages 3-8 will enjoy it the most.  Don’t forget the sunscreen and bring water to stay hydrated.

First Sunday Arts Festival

From May to December, Calvert & W Streets come alive for the First Sunday Arts Festival.  The pedestrian event features artists selling wares from glass bowls to tie dye t-shirts.  Entertainment in the form of music, dance and magic shows and there are food trucks galore.  Park next to the festival at the Whitmore Parking Garage and Gott’s Court Parking Garage on Calvert Street.  We came to also enjoy the festival and patiently waited to enter the downtown area due to the crowds.

There are many great places to grab a bite to eat!  If you’ve got a favorite, leave a comment below.

Masons Famous Lobster Rolls
188 Main St.

When in Annapolis, eating seafood is not a suggestion it’s a requirement.  In the past, I’ve dined at Buddy’s Crabs & Ribs and O’Brien’s Oyster Bar and Restaurant.  This time, the family wanted to dine al fresco and Masons Famous Lobster Rolls made the cut for my husband and I.  There are several choices and I was satisfied with the $14 Connecticut Roll which was simply lobster chunks served warm with butter with a side of Cape Cod chips.  Littles can order grilled cheese or a hot dog at $4 each, but bigger appetites may like the lobster grilled cheese at $10.

Chick & Ruth’s Delly
165 Main St.

I really wanted to visit Chick & Ruth’s Delly, especially since I saw it on an episode of Man v. Food.  Yet I couldn’t convince my husband to go there.  What I find unique about them is that the Pledge of Allegiance is recited every morning.  Their extensive menu includes breakfast served all day, made-from-scratch pies and a 6 pound milkshake.  Holy cow!

Ice cream is a big deal along Ego Alley.  There are about a half dozen options for ice cream in downtown Annapolis!  It wouldn’t be right if I didn’t try a sampling of what some of the competition has to offer.

Annapolis Ice Cream Company
196 Main St.

Meet the ice cream shop voted as the best in Annapolis.  Could it be that they use 17% butterfat making their cream so lip smacking good?  The reason could be the enormous gallery of artsy spoons checking in at 80,000 strong as of last year.  Kids and fans alike can decorate their own spoon to add to the Annapolis Ice Cream Company collection.  Stuffed penguins gaze over rotating daily flavors such as Banana Chocolate Chip, Cinnamon or Vanilla Heath Bar.

Capital Cakes & Cream
188 Main St.

Move over Cookie Monster.  Meet the ice cream cookie sandwich.  At $2.95, this is the best value in town.  I sampled Strawberry Pretzel Salad and Caramel Truffle, which were both good.  I ultimately went with Pineapple ice cream nestled between a macadamia nut and a triple chocolate cookie.  What sold me is that the cream is farmed from Bridgeville, DE and is non-homogenized, hormone and antibiotic free.

Storm Bros. Ice Cream Factory
130 Dock St.

The Storm Brothers are what ice cream dreams are made of.  Now in their 41st year, the homemade flavor menu features 46 flavors including Creamsicle, Junior Mint, and Superman.  You can also get soft serve, sugar free, floats, sorbet and frozen yogurt.  Bring the Benjamins as they only accept cash.

Not only is Main Street the area for great food, there are some shops that beckon you to enter. The Historic Annapolis Museum Store located near the Waterfront is great to find local gifts.  Kids and adults alike will have fun trying on fashion forward clothing at Hats in the Belfry.  My daughter has been into graphic novels lately so a visit to Capital Comics was a must.


We lucked out and found metered street parking right by the Dock.  The caveat is the max is a 2 hour stay.  You can pay the $2 per hour fee with credit, coins or phone app.  There is also a parking garage just off Main Street.

Other points of interest
Beyond the historic downtown area, Annapolis also has some other activities for families.

Quiet Waters Park
600 Quiet Waters Park Rd.

The name rings true.  Quiet Waters is a quiet, serene park where you’ll find flowering trees, fountains, hiking trails, playgrounds, picnic areas and a pedestrian bridge leading to a gazebo.  Rent bicycles, canoes, kayaks and pedal boats at South River, take in an outdoor concert in the summer and ice skating in the winter.  Cost is $6 to enter, $30 for an annual pass; $40 if you’re not a Maryland resident and free for military.  Cash is the only form of payment accepted to enter the park.  Make your first stop the visitor center to pick up a map of the area.  Note:  the park is closed on Tuesdays.

Sandy Point State Park

If you want to go to the beach, but don’t want the hassle of crossing the Bay Bridge, venture to Sandy Point State Park.  Weekday admission from May-September is $4 for Maryland residents and $6 for out of state visitors.  On the weekends and during holidays the price is $5 and $7 per vehicle.  Head out early to this bay beach, but beware of jellyfish.

The Bottom Line
Historic Annapolis is great for nautical lovers or people who want to experience a charming town while learning a little history.  It’s a sleepy town meaning many businesses close early with some closed on Mondays.
Photos courtesy of Kathleen Molloy.

Photo of author

OK Editorial Team

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