Annapolis isn’t just Maryland’s charming capital- its an incredible outdoor destination. As a local, I’ve spent countless days exploring the trails, paddling the creeks and indulging in some of the best seafood in the area.
If you’re looking for a scenic hike, a peaceful paddle, or a great meal after a day outside, this guide has you covered. I’ll share the best trails to explore, the top spots to get on the water, and my favorite local restaurants to refuel after your adventure.
Best Places to Hike (and Stroll) in Annapolis
Annapolis is widely known for its waterfront city and affiliation with the Naval Academy, but it also has some fantastic trails for those looking to get outdoors. Quiet Waters Park is a local favorite with scenic overlooks of the South River. With plenty of parking, a visitors center, and even a dog beach, this is the best place to spend an afternoon. The paved trails will lead you to a peaceful waterfront view, perfect for a quiet break. This park also shows up further down in this article because of their amazing kayak launch and rentals.
For a little more solitude and quiet trails, I would recommend Bacon Ridge Natural Area. There is a network of trails through the conservation area. Be sure to download a map before venturing out because these trails have a lot of intersections. Even if you don’t, these trails are well-marked and well-maintained. It’s a beautiful way to spend some time in nature without venturing far from Annapolis.
Greenbury Point Trail is another must-visit hike. It’s a 3 mile mostly flat walk to beautiful views of the Chesapeake Bay and iconic Naval Academy.
If you’re up for a short drive across the Bay Bridge, Terrapin Park is a little hidden gem on Kent Island. The trail winds through marshlands and opens up to a stunning beach with views of the Bay Bridge. It’s honestly one of the best places to spend an afternoon. You can post up on the beach all day, and never get bored.
A walk through Downtown Annapolis isn’t a traditional hike, but it’s just as fun. Stroll down Main Street. Stop in the charming coastal shops, take in the waterfront views and all of the history. For an even better time, walk over the bridge to Eastport, where you’ll get a beautiful view of the harbor and skyline- perfect for sunset!
Best Places to Paddle in Annapolis
You can’t visit Annapolis without getting on the water. Ok, you can, but I wouldn’t recommend it! Annapolis is a coastal town, and the best way to experience it is on a kayak or Stand up Paddle (SUP).
My top recommendation is Capital SUP at Quiet Waters Park. This spot is always good for a calm, scenic paddle. Bring your own, or rent a kayak on the dock- either way, you’re in for an amazing time. With lots of wildlife and epic views, it’s really one of those places where you can unwind. Bonus tip: schedule your paddle around their Summer Concert Series at the park, and listen to some tunes from the water!
For a more urban paddling experience, you’ve gotta go with Capital SUP- Eastport in Annapolis Harbor. It’s such an incredible experience to paddle around the harbor and soak up the waterfront views. You can paddle past the Naval Academy, and near the historic boats. You can also take in the sunset from here, which is one of my favorite places to watch from!
Explore the charming Spa Creek at Paddle Annapolis. It’s the perfect outfitter to float along the quiet coves and open waters around Downtown Annapolis. Book a guided tour to learn more about one of the oldest cities in America!
Bring your furry BFF along at Woof on the Wharf on the South River. This is a fantastic option if you refuse to leave your fur baby at home. The calm waters are perfect for paddling with your dog, and it’s a great place to unwind and get some fresh coastal air.
Best Places to Eat in Annapolis
Top Seafood Spots in Annapolis
After a long day outdoors, nothing beats a good meal and Annapolis has you covered. If you want to experience Maryland seafood (the best kind), you’ve gotta try Buddy’s Crabs & Ribs. Buddy’s is the classic choice for steamed crabs, oysters and all the Maryland favorites.
For a more upscale experience, The Chart House is the best bet for some of the best elevated seafood dishes in the area. This place also has beautiful views of the harbor.
Latitude 38 is another great option, with a mix of seafood and other creative dishes in a laid back, but posh setting.
Casual & Waterfront Dining in Annapolis
For a more casual meal, Boatyard Bar & Grill is one of my go-to spots. They have a great atmosphere and some delicious crab cakes.
Dock Street Bar & Grill is another solid choice, perfect for grabbing a bite downtown after exploring Main street and the City Dock.
If you’re looking for some Travel Channel fame, you have to check out Chick & Ruth’s Delly. This place is an Annapolis Institution, with signed photos of celebrities on the wall and a legendary reputation. They are known for their massive sandwiches, old school vibes and eating challenges.
Best Coffee & Tea Spots in Annapolis
As someone who always needs a coffee, my top pick is Bitty & Beau’s. Not just for great coffee, but also for their mission of employing individuals with disabilities.
Rise Up Coffee at City Dock is another favorite. I spent so many of my college days here drinking coffee and studying. They serve up some local coffee brews and the absolute best people watching.
Reynolds Tavern is not your average tea house. Reynolds is a local favorite for elegant afternoon teas- complete with cream teas and tiny sandwiches. History and elegance merge here for an unforgettable experience. My family loves coming here for special occasions.
Must-Stop Treat: Storm Bros Ice Cream
No trip to Annapolis is complete without a stop at Storm Bros Ice Cream. Its a local favorite for a reason- the BEST ice cream. Its conveniently located at the City Dock, so you can grab your cone and watch the sunset. Its the perfect way to end your day in Annapolis, Maryland.
Conclusion: Your Ultimate Annapolis Adventure
Annapolis is the perfect blend of outdoor adventure, waterfront charm, history and elegance. There’s no shortage of ways to spend the day here in this beautiful city.
As a local, I keep coming back to experience even more that this place has to offer.
I hope this guide helps you plan your Annapolis experience the way I do- through the trails, waterways and eats!
Have a favorite Annapolis spot I didn’t mention? Let me know in the comments or tag me in your adventures on Instagram—I’d love to see where you explore!
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