A Guide To All the Things To Do in Annapolis

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Last Updated on April 1, 2024 by Rick Spiegel

Once in a while, escaping from your mundane everyday life is good for your soul. That is to say, pack your bags and go somewhere. Oh, you’re already there? Well, that was quick & Annapolis is lovely this time of the year. Since you already know where to go, let’s talk about the things to do in Annapolis.

“The world is a book, and those who don’t travel have only read one page.” Wise words & true nonetheless. However, let’s start with a bit of information about your destination.

A Bit on Nap town

Known affectionately as Crabtown for its fascination with crab as a food source. In case you’re not convinced, they celebrate The Annapolis Rotary Crab Feast every year. Also, according to estimates, the city of Annapolis consumes about four million crabs per year.

But enough with the crabs, there is a lot more to this city than meets the eye, for instance:

  • Annapolis was the first Capital of the United States of America.
  • In addition to Crabtown, it’s also known as the Sailing Capital of the U.S.
  • And the Naval Academy is situated in Annapolis, etc.

So, moving on, let’s discuss the best time to visit the city of Annapolis.

Things to Do in Annapolis – An Itinerary

So, now let’s discuss all the fun things to do in Annapolis with your partner or your whole family. Also, if you’re a lone traveler, lucky you because most of these activities are fun even alone.

Things to Do for Couples

Kent Island Cross Island Trail

Ride to the Old Love Point Park through the Kent Island Cross Trail with your beloved. Experience the beautiful view & wildlife along the 9.2 miles long cross-island trail. In addition to riding, this trail is also available to trekkers & skaters, and it’s also wheelchair accessible.

End PointTerrapin Nature Area Kent Island
NavigationTrail Map
Length9.2 Miles

Go-Kart Racing

There’s something inherently fun about competing in motorsports like Go-Kart racing. So, wouldn’t it be even better to enjoy such an adrenaline-filled sport with your significant other? Therefore, we recommend you visit the Crofton Go-Kart Raceway and enjoy speeding laps around the ½ mile-long track.

Location1050 State Route 3 South (1050 Crain Hwy)
Gambrills, MD 21054
(410) 721.2900
TimingWeekdays – 3 PM to 8 PM, Weekends – 10 AM to 10 PM
Prices$3.40 – $150.00 per person
Contact Information410-721-2900

Catch Popular Plays at the Annapolis Summer Garden Theatre

Few things stimulate the mind as a great form of art. So, why enjoy it all alone? Go out with your partner to the Summer Graden Theatre. And catch exhilarating performances of musicals like,

  • Rock of Ages
  • Bright Star
  • The Drowsy Chaperon
LocationAnnapolis Summer Garden Theatre
143 Compromise Street
Annapolis, MD 21401
Timing08:30 PM
Prices$27 per person
Contact Information410-268-9212

Schooner Woodwind Yacht Racing

Become part of the Wednesday night yacht racing at the Schooner Woodwind Yacht Racing event. Enjoy the beautiful view of Annapolis from a 74-foot long while enjoying the cool ocean breeze.

In addition to the ambiance, feast on a wide variety of food items on your cruise.

Prices$71.95 – $75.25
Contact Information410-263-7837

Also read: Things To Do In San Diego

Picnic at Sandy Point State Park

Pack your basket & head out to Sandy Point State Park for a nice picnic with your beloved. And enjoy the beautiful view of the Bay Bridge from your favorite spot. In case you forget to carry your mat, don’t worry, you’ll find a number of picnic tables to relax.

Location1100 E College Pkwy, Annapolis, MD 21409
Timing7 AM to Dusk
Contact Information410-974-2149

Activities for Kids

Towne Transport Trolley Tour

Enjoy sightseeing with your kids on the Annapolis’ free trolly service. To get on the ride, just track it through here.

On the other hand, you can also book trolley tours with Towne Transport.

Location26 West Street Annapolis, MD 21401
Timing10;30 AM to 3 PM
Prices$18 per person
Contact Information410-626-6000

Quiet Waters Park

Go out for an excellent picnic day with your kids at the Quite Waters Park. Also, the park is a 14-minute drive from the Lee Airport (ANP). In addition to the picnic, your kids can also enjoy the playground. At the same time, you can enjoy the serene view of the magnificent grasslands.

The park is around 340 acres in size, right at the sea’s edge.

Location600 Quiet Waters Park Rd, Annapolis, MD 21403, United States
Timing7 AM to 8 PM
PricesNo Charge
Contact Information+1 410 222 1777

Enjoy the Famous Kilwins Chocolates & Ice Creams

We all know how kids can be; one minute they are running around, and the next crying for food. And sweets, don’t get us started; those little runts can eat a whole box of chocolates.

Therefore, we’d recommend you visit the Kilwins Ice Cream a block north of the Ego Alley. And sit & relax with your partner with a cup of coffee; you deserve it.

Location 128 Main St. Annapolis, MD 21401 United States
Timing10 AM to 10 PM
Prices$1.17 – $59.99 per item
Contact Information410-263-2601

Pirate Adventures on the Chesapeake

Above all, if we know anything about kids, they love to play make-believe. For instance, imagine your little bundle of joy with an eye patch going “Argh!” And we bet it’d be pretty amazing for them to celebrate their birthday with a costume party on a cruise.

Although, don’t hand them a real sword for the sake of authenticity.

LocationPirate Adventures on the Chesapeake
311 Third Street
Annapolis MD 21403
Timing10 AM, 12 AM, 2 PM, 4 PM
Prices$28 per person
Contact Information410 263 0002

The Chesapeake Children’s Museum

Lastly, running around is fun, but boring things like education are essential too. Thus, we implore you to visit The Chesapeake Children’s Museum with your kids. In addition to some learning, your kids also get to participate in fun team activities, like-

  • Girls Scouts
  • Creek Critters Nature Walk
  • La Cocina Latina (Cooking Class), etc.
Location25 Silopanna Road, Annapolis, MD 21403
Timing10 AM to 03:30 PM
Prices$8.20 per person
Contact Information410 990 1993

Festivals to Enjoy with the Whole Family

Annapolis Rotary Crab Feast

Most importantly, you must enjoy the most famous occasion celebrated in Annapolis, the Rotary Crab Feast. Annapolis isn’t known as the Crabtown for nothing; the feast is all you can eat/drink.

To summarize, this is the world’s largest crab feast; as we said, Annapolis is obsessed with crabs. In addition, the proceeds from the feasts go towards the local community & cultural organizations.

LocationNavy-Marine Corps Memorial Stadium, 550 Taylor Ave, Annapolis, MD 21401
Timing5 PM to 8 PM,
August 5th, 2022
 $90 – $180 per person
Contact Information

Maryland Renaissance Festival

Travel back in time & experience the wonders of the Renaissance period; visit the Maryland Renaissance Festival. In addition to the ambiance, enjoy a variety of cuisines & merchandise.

Also, participate in special events like – Pirate Adventure Weekend, Shakespeare Weekend, American Sign Language Interpretation Days, etc.

Location1821 Crownsville Road,
Annapolis, MD 21401
Prices$10 – $21 per person
Contact Information(410) 266-7304

United States Sailboat Show

In short, enjoy the ultimate sailing experience with amateur & veteran soldiers from all around the globe. Gathered around miles of docks on the historic Annapolis downtown.

LocationCity Dock, Annapolis, MD  
Timing10:00 AM to 06:30 PM
Prices$40 – $60
Contact Information410 268 8828

Eastport Yacht Club Lights Parade

In order to experience the majestic beauty of the night sea, visit the Light Parade at Eastport Yacht Club. Watch brightly lit boats appear out of nowhere from the horizon of the dark, cold waters. So, don’t wait around and participate in this Annapolis tradition.

Location317 First St, Annapolis, MD 21403, United States
Timing06:00 PM to 08:00 PM, December 10th, 2022
Contact Information410 268 8828

Annapolis Chocolate Binge Festival

Lastly, who doesn’t like chocolate? No hands, just like we expected. Whether it is for your consumption or you’re just interested in the history of chocolate. Then, the Annapolis Chocolate Binge Festival is for you.

In addition to chocolates, you can also find other events like gluten-free, organic, and Non-GMO at this fest. So, what are you waiting for?

LocationCity Dock, Annapolis, MD  
Timing11 AM to 5 PM, December 4th, 2022
Contact Information[email protected]

So, now that you know the things to do in Annapolis let’s answer some of your queries.

Frequently Asked Questions(FAQs)

What’s Annapolis famous for?

In short, there are many things of beauty & importance in Annapolis. However, the most famous site in Annapolis is the United States Naval Academy.

Is Annapolis worth visiting?

Annapolis is a small yet beautiful town with a lot of historical sites. So, to answer your question, yes, the city of Annapolis is definitely worth a visit.

Is the Naval Academy open for tours?

In short, yes, the Naval Academy is open for a public tour year-round. However, your group must not consist of more than 15 people.

How do I spend a day in Annapolis?

If you are visiting Annapolis for the first time, then you can spehe your day by spending your time by visiting Annapolis Historic District,  U.S. Naval Academy, and Quiet Waters Park.

Is Annapolis worth a visit?

Yes, it is worth visiting Annapolis. You can go to this place to explore its architecture. Not only this, but you can relax, shop, and dine with your family and friends.

What is Annapolis best known for?

Annapolis is known as the “Sailing Capital of the U.S.” and home to the U.S. Naval Academy. Also, Annapolis’s maritime heritage is merged with its cosmopolitan flair to create a destination that is worth visiting.

Is Annapolis a party town?

Yes, Annapolis is a party town. As the sun sets, to the Annapolis streets for an amazing night. You can drink, dance, and enjoy the lively atmosphere from Dock Street to West Street.

Is Annapolis safe to walk around?

Yes, it is safe to walk around in Annapolis. This place is ranked in the 20th percentile when comes to crime safety. Moreover, around 80% of the U.S. cities are safer. So, you can enjoy visiting different places in Annapolis without any fear.

Is Baltimore or Annapolis better to visit?

It depends on your preferences and requirements. There is no doubt that Baltimore is large and has more dining and going options. But it is not a shopping destination. Moreover, if you prefer crowds and love having parties, then you must visit Annapolis.

What kind of food is Annapolis known for?

Food plays an important role in the travel industry. So, if you are going to explore Annapolis, then you must try the  Chesapeake Bay seafood and signature dishes, especially the crab cakes, blue crabs, and star if crab feasts.

Why is Annapolis so Irish?

In the 1600s, Annapolis began as a shipping port and the watermen were Irish. Som the name name of Baltimore came from the  Irish Bal ne Tighe Mor and later it was named for Ceclius Calvert.

How much does it cost to tour the Naval Academy?

If you are going to visit it Naval Academy in Annapolis, then make sure all the visitors are 18 years and older. Plus, you must carry your government-issued ID cards. Also, the guided public tour will cost around $12 per adult; $11 for seniors 

Is Annapolis safe at night for tourists?

Yes, Downtown Annapolis and the Naval Academy area are safer for tourists to explore the place at night. However, it is advised not to walk alone in late night.

Where is Main Street in Annapolis?

The main street in Annapolis is located between the Church Circle and City Dock. You should explore the busy sidewalks, the beautiful view of the Annapolis Harbor, and the bustling shops. Moreover, Main Street is a great point to start your day in Annapolis.

How expensive is Annapolis MD?

Annapolis is quite expensive when it comes to housing expenses and utility prices. The utility prices are 5% higher than the national average and housing expenses are 142% higher than the average. Moreover, transportation expenses such as bus fares and gas prices are also 1% higher than the national average.

Is Annapolis a military town?

Yes, Annapolis is a military town. The Naval Academy is situated in Annapolis, Maryland on the banks of the River- Severn. Also, the Naval area is composed of the  Naval Support Activity Annapolis,  U.S. Naval Academy, and other tenant commands.

How can I go to Annapolis from DC without a car?

You can get from Annapolis to DC without a car through a bus. You can take the Maryland Transit Administration bus for a comfortable commute from Annapolis to DC.

How do you get around Annapolis?

You can get around Annapolis through the public transport services via regular fixed routes, ADA Complimentary paratransit services, and a shuttle. Also, transit vehicles such as wheelchairs are accessible to needy tourists.


David Ross

I'm David Ross, an enthusiastic traveler and writer, deeply passionate about airline travel. My insatiable curiosity for exploring new destinations and my unwavering commitment to assisting fellow travelers in navigating the intricacies of air travel have brought me here to share my knowledge with you. Drawing from my extensive experience in the aviation industry, I've made it my mission to create detailed airline travel guides to ensure your journeys are as hassle-free as possible.

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