Things To Do In Annapolis | Annapolis Travel Guide

Last Updated on October 10, 2023 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 Point	Terrapin Nature Area Kent Island
Navigation	Trail Map
Length	9.2 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.

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

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

Location	Annapolis Summer Garden Theatre 143 Compromise Street Annapolis, MD 21401
Timing	08:30 PM
Prices	$27 per person
Contact Information	410-268-9212

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.

Timing	Variable
Prices	$71.95 – $75.25
Contact Information	410-263-7837

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.

Location	1100 E College Pkwy, Annapolis, MD 21409
Timing	7 AM to Dusk
Prices	Free
Contact Information	410-974-2149

Activities for Kids

Towne Transport Trolley Tour

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

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

Location	26 West Street Annapolis, MD 21401
Timing	10;30 AM to 3 PM
Prices	$18 per person
Contact Information	410-626-6000

Quiet Waters Park

Go out for an excellent picnic day with your kids at the Quite Waters Park. Also, the park is a 14 minutes 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.

Location	600 Quiet Waters Park Rd, Annapolis, MD 21403, United States
Timing	7 AM to 8 PM
Prices	No 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, 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
Timing	10 AM to 10 PM
Prices	$1.17 – $59.99 per item
Contact Information	410-263-2601

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 “Arrrrgh!” 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.

Location	Pirate Adventures on the Chesapeake 311 Third Street Annapolis MD 21403
Timing	10 AM, 12 AM, 2 PM, 4 PM
Prices	$28 per person
Contact Information	410 263 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.

Location	25 Silopanna Road, Annapolis, MD 21403
Timing	10 AM to 03:30 PM
Prices	$8.20 per person
Contact Information	410 990 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.

Location	Navy-Marine Corps Memorial Stadium, 550 Taylor Ave, Annapolis, MD 21401
Timing	5 PM to 8 PM, August 5^th, 2022
	$90 – $180 per person
Contact Information	https://www.annapolisrotary.org/crabfeast

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.

Location	1821 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.

Location	City Dock, Annapolis, MD
Timing	10:00 AM to 06:30 PM
Prices	$40 – $60
Contact Information	410 268 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.

Location	317 First St, Annapolis, MD 21403, United States
Timing	06:00 PM to 08:00 PM, December 10^th, 2022
Contact Information	410 268 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, 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?

Location	City Dock, Annapolis, MD
Timing	11 AM to 5 PM, December 4^th, 2022
Prices	N.A.
Contact Information	firstsundayarts @ yahoo.com

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

Frequently Asked Questions

Q1. 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.

Q2. 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.