9 Activities
Road Trip to Annapolis: Maryland History, Seafood, and the Chesapeake Bay
Starts from
Washington
Transportation
By Car
Guidance
Self-Guided
Activities
9
Duration
11 hours
Length
45 mi
Guide details
Starts from
Washington
Transportation
By Car
Guidance
Self-Guided
Duration
11 hours
Length
45 mi
Adrienne Mahsa Varkiani
Travel Expert
- As Maryland's capital city, Annapolis is full of beautiful views and history.
- The Chesapeake Bay is known for its crabs. Order it everywhere you go on this trip.
- Wear comfortable shoes as you'll be doing lots of walking.
Explore Maryland's capital city and other smaller towns as you drive across the Chesapeake Bay.
This route is a scenic one, with plenty of stops at parks, beaches, and a boat ride across the bay. Maryland is known for its Chesapeake blue crabs, and this route also contains stops to try seafood right from the source. You won't get any of this in the city.
This route is a scenic one, with plenty of stops at parks, beaches, and a boat ride across the bay. Maryland is known for its Chesapeake blue crabs, and this route also contains stops to try seafood right from the source. You won't get any of this in the city.
Explore Maryland's capital city and other smaller towns as you drive across the Chesapeake Bay.
This route is a scenic one, with plenty of stops at parks, beaches, and a boat ride across the bay. Maryland is known for its Chesapeake blue crabs, and this route also contains stops to try seafood right from the source. You won't get any of this in the city.
This route is a scenic one, with plenty of stops at parks, beaches, and a boat ride across the bay. Maryland is known for its Chesapeake blue crabs, and this route also contains stops to try seafood right from the source. You won't get any of this in the city.
Adrienne Mahsa Varkiani
Travel Expert
- As Maryland's capital city, Annapolis is full of beautiful views and history.
- The Chesapeake Bay is known for its crabs. Order it everywhere you go on this trip.
- Wear comfortable shoes as you'll be doing lots of walking.
Day Itinerary
9 Activities
Day 1
45 mi0.8 mi
Bayside Exploring and Seafood
The real "Bay Area" is on the East Coast. The Chesapeake Bay is the largest estuary in the country.
On this trip, you'll visit a park by the bay, go sailing down the Bay, and eat lots and lots of seafood.
On this trip, you'll visit a park by the bay, go sailing down the Bay, and eat lots and lots of seafood.
10:0045 min
Pennsylvania Dutch Farmer's Market
Farmers Market
Open Details
Start your day off right: with snacks from the Pennsylvania Dutch Farmer's Market.
Known locally as the "Amish Market," this giant market has everything you could need for your road trip. All the products come from Pennsylvania's Lancaster County, and the recipes here have been handed down by the Amish through the generations.
There will be a fair amount of walking on this trip, so get some light snacks you can carry with you in case you get hungry later in the day. Stock up on produce, desserts, cheese, candy, or whatever else your heart desires. Many people rave about the fresh-baked pretzels in particular.
Known locally as the "Amish Market," this giant market has everything you could need for your road trip. All the products come from Pennsylvania's Lancaster County, and the recipes here have been handed down by the Amish through the generations.
There will be a fair amount of walking on this trip, so get some light snacks you can carry with you in case you get hungry later in the day. Stock up on produce, desserts, cheese, candy, or whatever else your heart desires. Many people rave about the fresh-baked pretzels in particular.
10.8 mi
15 min
11:005 min
Chesapeake Bay Bridge
Bridge
Open Details
You'll be driving across the Chesapeake Bay to get to Kent Island. Make sure to have your camera ready—the photos will be worth it.
6.7 mi
15 min
11:201 hr 30 min
Terrapin Nature Park
Nature Preserve
Open Details
This 276-acre nature park isn't as crowded as it should be given all that it offers.
There is a 3.25-mile oyster chaff walking trail, which takes you through marshlands, woodlands, and sandy beaches. You can also bike or kayak here, if you want something a bit more active.
Thanks to the diversity of habitats here, this park is great for bird-watching. It is the top hotspot in Queen Anne’s County in terms of the number of bird species reported.
This park doesn't have a public beach for swimming. If that's what you're looking for, try the Matapeake Clubhouse and Beach nearby.
There is a 3.25-mile oyster chaff walking trail, which takes you through marshlands, woodlands, and sandy beaches. You can also bike or kayak here, if you want something a bit more active.
Thanks to the diversity of habitats here, this park is great for bird-watching. It is the top hotspot in Queen Anne’s County in terms of the number of bird species reported.
This park doesn't have a public beach for swimming. If that's what you're looking for, try the Matapeake Clubhouse and Beach nearby.
6.5 mi
15 min
13:151 hr 30 min
Kentmorr Restaurant
Seafood Restaurant
Open Details
Maryland is known for crab and crab cakes, and this is the place to try both.
This waterfront restaurant faces the Chesapeake Bay, so you can enjoy the view while you eat. In the spring and summer, Dirty Dave's Tiki Bar serves up cold beer and frozen drinks right on the beach.
If crab isn't for you, you can try one of the brick oven pizzas, steamed shrimp, or any of the fish entrees.
This waterfront restaurant faces the Chesapeake Bay, so you can enjoy the view while you eat. In the spring and summer, Dirty Dave's Tiki Bar serves up cold beer and frozen drinks right on the beach.
If crab isn't for you, you can try one of the brick oven pizzas, steamed shrimp, or any of the fish entrees.
20.3 mi
40 min
15:301 hr 30 min
Watermark Journey
Travel Agency
Open Details
Watermark offers seven different cruises in Annapolis, with different lengths and destinations.
If you're not sure what you're looking for, try the Annapolis Harbor and U.S. Naval Academy cruise. This narrated cruise will leave you with a better understanding of Annapolis’ role as a historic seaport and the history of the Naval Academy. You'll also catch another glimpse of the Bay Bridge, this time from a different angle.
If it's later in the day, you should do the Annapolis Sunset Cruise. This 60-minute cruise through the harbor will be beautiful.
Watermark is closed on Saturdays, but you should be able to find another cruise option as you explore Annapolis.
You can book a tour in advance.
After the cruise, leave your car here and explore the city on foot.
If you're not sure what you're looking for, try the Annapolis Harbor and U.S. Naval Academy cruise. This narrated cruise will leave you with a better understanding of Annapolis’ role as a historic seaport and the history of the Naval Academy. You'll also catch another glimpse of the Bay Bridge, this time from a different angle.
If it's later in the day, you should do the Annapolis Sunset Cruise. This 60-minute cruise through the harbor will be beautiful.
Watermark is closed on Saturdays, but you should be able to find another cruise option as you explore Annapolis.
You can book a tour in advance.
After the cruise, leave your car here and explore the city on foot.
0.2 mi
5 min
17:1010 min
Kunta Kinte-Alex Haley Memorial
Landmark
Open Details
Alex Haley was a prominent Black writer, most famous for his best selling novel Roots, which won national acclaim. The story follows Kunta Kinte, an 18th-century captured from Gambia as a child, sold into slavery in Africa, and later transported to North America. It details Kinte's life as well as his descendants—all the way to Haley himself.
In the story, the slave ship on which Kinte is entrapped lands in Annapolis, Maryland—hence the location of this memorial.
Like many other monuments to Black leaders and Black history in America, the Kunta Kinte-Alex Haley Memorial has faced an uphill battle. A group of Annapolis residents initially proposed the idea of a memorial to city council in 1979, but were met with opposition from Annapolis' mayor. Two years later, with a new mayor in office, a plaque was set up at the City Dock in commemoration of Kinte's arrival in 1767. But according to the Kunta Kinte-Alex Haley Foundation, the plaque was stolen just two days later.
The memorial in downtown Annapolis today was not completed until 2002, nearly 30 years after Roots was published. Haley did not live long enough to see this memorial.
In the story, the slave ship on which Kinte is entrapped lands in Annapolis, Maryland—hence the location of this memorial.
Like many other monuments to Black leaders and Black history in America, the Kunta Kinte-Alex Haley Memorial has faced an uphill battle. A group of Annapolis residents initially proposed the idea of a memorial to city council in 1979, but were met with opposition from Annapolis' mayor. Two years later, with a new mayor in office, a plaque was set up at the City Dock in commemoration of Kinte's arrival in 1767. But according to the Kunta Kinte-Alex Haley Foundation, the plaque was stolen just two days later.
The memorial in downtown Annapolis today was not completed until 2002, nearly 30 years after Roots was published. Haley did not live long enough to see this memorial.
0.3 mi
10 min
17:301 hr 30 min
Colonial Annapolis Historic District
City Centre
Open Details
In 1965, Annapolis became one of the first cities to become a National Historic Landmark District. This status covers most of the colonial historic district as well as the waterfront.
Many 18th-century buildings still stand here, including historic residences, townhouses, and the Maryland State House, which is nearby. The State House is the oldest state capitol in continuous legislative use and the only one ever used as the nation's Capitol.
This is also a great area to just explore, with many restaurants and shops you can spend your afternoon getting lost in.
Many 18th-century buildings still stand here, including historic residences, townhouses, and the Maryland State House, which is nearby. The State House is the oldest state capitol in continuous legislative use and the only one ever used as the nation's Capitol.
This is also a great area to just explore, with many restaurants and shops you can spend your afternoon getting lost in.
0.4 mi
10 min
19:105 min
Watermark Journey
Travel Agency
Open Details
Return to pick up your car and head to the dinner restaurant.
0.9 mi
10 min
19:301 hr 30 min
Boatyard
Seafood Restaurant
Open Details
This seafood restaurant has everything you could want: crab, crab cakes, crab soup, oysters, shrimp, mussels, fish of the day, and more.
This restaurant is small, further away from the crowded Main Street, and always packed because of how great the food is. If you ate crab for lunch, it doesn't matter—order it again here. It's delicious.
This restaurant is small, further away from the crowded Main Street, and always packed because of how great the food is. If you ate crab for lunch, it doesn't matter—order it again here. It's delicious.