Food scene
Davis's Pub
400 Chester AveWithin walking distance, great little pub!
Boatyard Bar & Grill
400 Fourth StWithin walking distance, fun atmosphere and awesome food!
Chart House
300 Second StWithin walking distance, up scale restaurant with amazing food.
Great local place for breakfast, lunch or dinner. Diner style dining. Their milkshakes are a must try!
60 locals recommend
Chick & Ruth's Delly
165 Main StGreat local place for breakfast, lunch or dinner. Diner style dining. Their milkshakes are a must try!
Carrol's Creek Cafe
410 Severn AveIron Rooster - Annapolis
12 Market SpaceAmazing breakfast, located Downtown Annapolis.
A true Annapolis landmark, George Washington, Thomas Jefferson and Benjamin Franklin were numbered among its prominent patrons.
34 locals recommend
Middleton Tavern
2 Market SpaceA true Annapolis landmark, George Washington, Thomas Jefferson and Benjamin Franklin were numbered among its prominent patrons.
A hidden gem with amazing brick oven pizza! Located on Main Street in Downtown Annapolis
44 locals recommend
Fox's Den
179B Main StA hidden gem with amazing brick oven pizza! Located on Main Street in Downtown Annapolis
A unique place that is defiantly a locals favorite! Heads up, if you plan on dinning here on the weekend get there early to get a table.
126 locals recommend
Vin 909 Winecafe
909 Bay Ridge AveA unique place that is defiantly a locals favorite! Heads up, if you plan on dinning here on the weekend get there early to get a table.
SHOPPING, DINING, LIVING, AND MUCH MORE
It's everything extraordinary—all in one sensational destination. A beautiful Towne Centre where you can shop, dine, live, work and play. Plus, it’s conveniently located less than four miles from downtown Annapolis. In addition to being anchored by premier lifestyle retailers and first-quality restaurants, this one-stop shopping center provides a sense of community where residents and visitors frequently come together for events like the summer concert and much more. Hassle-free onsite parking makes the decision to come to Annapolis Towne Centre even easier.
43 locals recommend
Annapolis Towne Centre
1906 Towne Centre BlvdSHOPPING, DINING, LIVING, AND MUCH MORE
It's everything extraordinary—all in one sensational destination. A beautiful Towne Centre where you can shop, dine, live, work and play. Plus, it’s conveniently located less than four miles from downtown Annapolis. In addition to being anchored by premier lifestyle retailers and first-quality restaurants, this one-stop shopping center provides a sense of community where residents and visitors frequently come together for events like the summer concert and much more. Hassle-free onsite parking makes the decision to come to Annapolis Towne Centre even easier.
Leeward Market | Café & Grocery
601 Second StQuick stroll for coffee, breakfast and lunch!
Sightseeing
Hail the water taxi, take a walk or drive (parking can be challenging)....Downtown Annapolis is a must see and do!
Historic downtown Annapolis is a vibrant, thriving 21st-century neighborhood with 18th-century charm. A walk down Main Street puts you in touch with four centuries of architecture lovingly preserved. There's a contagious energy in the air here that some call addictive. Look in any direction and you'll find something to pique your imagination - eye catchers including the Chesapeake Bay, Midshipmen in dress whites, historic landmarks, shops, and restaurants of every size and description. And that's just for starters! Located between Church Circle and City Dock, Main Street can’t be missed with its ever-busy sidewalks, views of the Annapolis Harbor, and bustling shops.
209 locals recommend
Annapolis
Hail the water taxi, take a walk or drive (parking can be challenging)....Downtown Annapolis is a must see and do!
Historic downtown Annapolis is a vibrant, thriving 21st-century neighborhood with 18th-century charm. A walk down Main Street puts you in touch with four centuries of architecture lovingly preserved. There's a contagious energy in the air here that some call addictive. Look in any direction and you'll find something to pique your imagination - eye catchers including the Chesapeake Bay, Midshipmen in dress whites, historic landmarks, shops, and restaurants of every size and description. And that's just for starters! Located between Church Circle and City Dock, Main Street can’t be missed with its ever-busy sidewalks, views of the Annapolis Harbor, and bustling shops.
Located directly across the street! Be sure to take in the amazing sunrise from the dock!
61 locals recommend
Annapolis Maritime Museum & Park
723 Second StLocated directly across the street! Be sure to take in the amazing sunrise from the dock!
HISTORY, SHOPPING, DINING ON MARYLAND AVE
Maryland Avenue is a perfect example of the out-of-sight—but not out-of-the-way—streets in Annapolis where you’ll find hidden shopping hubs. In the shadow of the Maryland State House, the quaint and windy street in downtown Annapolis offers visitors an unparalleled shopping experience. And it’s been doing so for quite some time.
Maryland Avenue
Maryland AvenueHISTORY, SHOPPING, DINING ON MARYLAND AVE
Maryland Avenue is a perfect example of the out-of-sight—but not out-of-the-way—streets in Annapolis where you’ll find hidden shopping hubs. In the shadow of the Maryland State House, the quaint and windy street in downtown Annapolis offers visitors an unparalleled shopping experience. And it’s been doing so for quite some time.
Looking for something bigger than the boutiques of downtown Annapolis? Head to Westfield Annapolis Mall, located about four miles from downtown Annapolis.
The elegant, upscale Westfield Mall boasts 1.5 million square feet housing more than 210 specialty shops and nationally known restaurants. From exclusive luxury retailers featuring women’s wear to electronics to houseware and so much more, you’re certain to find what you need—and maybe what you just plain old want. In addition to great shopping and plentiful dining options, Westfield Mall’s 11-screen Bow Tie Cinema provides entertainment for all.
If you're looking for locally grown produce, check out Westfield's seasonal weekend farmer's market. If you'd rather let someone else do the cooking, duck into one of the mall's many fine eateries. Enjoy!
95 locals recommend
Westfield Annapolis Mall
2002 Annapolis MallLooking for something bigger than the boutiques of downtown Annapolis? Head to Westfield Annapolis Mall, located about four miles from downtown Annapolis.
The elegant, upscale Westfield Mall boasts 1.5 million square feet housing more than 210 specialty shops and nationally known restaurants. From exclusive luxury retailers featuring women’s wear to electronics to houseware and so much more, you’re certain to find what you need—and maybe what you just plain old want. In addition to great shopping and plentiful dining options, Westfield Mall’s 11-screen Bow Tie Cinema provides entertainment for all.
If you're looking for locally grown produce, check out Westfield's seasonal weekend farmer's market. If you'd rather let someone else do the cooking, duck into one of the mall's many fine eateries. Enjoy!
Neighborhoods
DIFFERENT SIDE OF ANNAPOLIS
Take a water taxi from City Dock or shuffle across the Spa Creek Bridge to Eastport, the laid-back, maritime district of Annapolis.
Just the view of Annapolis makes the trip to the other side of the harbor worthwhile. Dotted with its iconic domes and spires, from the red-roofed brick buildings of the town to the stately copper-topped campus of the Naval Academy, it's a sight you won't see anywhere else in America. Eastport is where you can touch the Chesapeake - stick your toe in the water at one of the many street-end parks, rent a canoe or a kayak for a duck's-eye view of the Harbor, or get immersed in our watermen's heritage at the Annapolis Maritime Museum.
EASTPORT'S RESTAURANT ROW
Once you’re in Eastport, you can’t miss out on “Restaurant Row.” Boasting a couple of Annapolis’ favorite local dining spots serving up fresh seafood along with great steakhouses, it’s the perfect place to get away from the bustle of downtown. It’s also one of the only areas where you can dine right against the water, enjoying a great meal while catching the sun dipping behind Annapolis. With great food and live music along with rooftop and waterfront dining, Eastport is a great choice when looking for another side of Annapolis.
34 locals recommend
Eastport
DIFFERENT SIDE OF ANNAPOLIS
Take a water taxi from City Dock or shuffle across the Spa Creek Bridge to Eastport, the laid-back, maritime district of Annapolis.
Just the view of Annapolis makes the trip to the other side of the harbor worthwhile. Dotted with its iconic domes and spires, from the red-roofed brick buildings of the town to the stately copper-topped campus of the Naval Academy, it's a sight you won't see anywhere else in America. Eastport is where you can touch the Chesapeake - stick your toe in the water at one of the many street-end parks, rent a canoe or a kayak for a duck's-eye view of the Harbor, or get immersed in our watermen's heritage at the Annapolis Maritime Museum.
EASTPORT'S RESTAURANT ROW
Once you’re in Eastport, you can’t miss out on “Restaurant Row.” Boasting a couple of Annapolis’ favorite local dining spots serving up fresh seafood along with great steakhouses, it’s the perfect place to get away from the bustle of downtown. It’s also one of the only areas where you can dine right against the water, enjoying a great meal while catching the sun dipping behind Annapolis. With great food and live music along with rooftop and waterfront dining, Eastport is a great choice when looking for another side of Annapolis.