Guidebook for Annapolis
Food Scene
Featured on Guy Fieri's Diners, Drive-Ins, and Dives, Galway Bay is one of the best kept secrets in Annapolis. Say hi to our friends Christina, Haas, and Jess on the pub side and enjoy their fantastic Irish classics, fantastic crab cakes, local specialty beers made just for them, Sunday afternoon live music, Monday-night Burger night, or Wednesday night Mack-and-cheese night.
Diners, Drive-Ins, and Dives Galway Bay - YouTube:
https://www.youtube.com/watch?v=oEErOg5WtWM
50 locals recommend
Galway Bay Irish Restaurant and Pub
63 Maryland AveFeatured on Guy Fieri's Diners, Drive-Ins, and Dives, Galway Bay is one of the best kept secrets in Annapolis. Say hi to our friends Christina, Haas, and Jess on the pub side and enjoy their fantastic Irish classics, fantastic crab cakes, local specialty beers made just for them, Sunday afternoon live music, Monday-night Burger night, or Wednesday night Mack-and-cheese night.
Diners, Drive-Ins, and Dives Galway Bay - YouTube:
https://www.youtube.com/watch?v=oEErOg5WtWM
Iron Rooster is a regional chain with exceptional service and daily specials. They serve breakfast/brunch foods all-day/every-day so you don't have to fight the crowds on Sunday morning.
104 locals recommend
Iron Rooster - Annapolis
12 Market SpaceIron Rooster is a regional chain with exceptional service and daily specials. They serve breakfast/brunch foods all-day/every-day so you don't have to fight the crowds on Sunday morning.
O'Learys is a one-of-a-kind seafood restaurant with an incredibly good menu. Stop in and say hi to our friend Will (the owner). He will let you know exactly what to get, but you can't go wrong with whatever you choose. If you go for breakfast/brunch, don't forget to try the pancake battered bacon drizzled!
26 locals recommend
O'Learys Seafood Restaurant
310 Third StreetO'Learys is a one-of-a-kind seafood restaurant with an incredibly good menu. Stop in and say hi to our friend Will (the owner). He will let you know exactly what to get, but you can't go wrong with whatever you choose. If you go for breakfast/brunch, don't forget to try the pancake battered bacon drizzled!
Sailor Oyster Bar (SoB) is chic industrial-style bar and oyster bar. Fresh and incredible Chesapeake Bay oysters, beer/cocktails, and assorted sandwiches are a perfect lunch or light dinner. Plus, they are one of the few LGBT friendly places in town.
33 locals recommend
Sailor Oyster Bar
196 West StSailor Oyster Bar (SoB) is chic industrial-style bar and oyster bar. Fresh and incredible Chesapeake Bay oysters, beer/cocktails, and assorted sandwiches are a perfect lunch or light dinner. Plus, they are one of the few LGBT friendly places in town.
Named after the 85 extra days of prohibition "suffered" by residents of DC until the Sheppard Act was repealed in 1934, this bar has the best whiskey and bourbon selection you will probably ever find.
27 locals recommend
DRY 85
193 B Main StNamed after the 85 extra days of prohibition "suffered" by residents of DC until the Sheppard Act was repealed in 1934, this bar has the best whiskey and bourbon selection you will probably ever find.
Inspired by the Creole Food of the New Orleans French Quarter, this Wine-themed bar has everything from fresh beignets and a mimosa cart-bar, to the widest selection of wines in the area.
36 locals recommend
Red Red Wine Bar
189 B Main StInspired by the Creole Food of the New Orleans French Quarter, this Wine-themed bar has everything from fresh beignets and a mimosa cart-bar, to the widest selection of wines in the area.
Tucked away and nearly hidden, this a perfect family-owned spot to stop for breakfast or lunch. The staff are fantastic and friendly. Their Chicken Waffle Sandwich is just fantastic.
16 locals recommend
Bread and Butter Kitchen
303 Second StTucked away and nearly hidden, this a perfect family-owned spot to stop for breakfast or lunch. The staff are fantastic and friendly. Their Chicken Waffle Sandwich is just fantastic.
Only open for Breakfast and Lunch, this is truly a secret local's place. The very small dining area fills up quickly but you can call ahead when you're on your way to put your name on the wait list. Fantastic food and great service.
15 locals recommend
Evelyn's
26 Annapolis StOnly open for Breakfast and Lunch, this is truly a secret local's place. The very small dining area fills up quickly but you can call ahead when you're on your way to put your name on the wait list. Fantastic food and great service.
Drinks & Nightlife
Dock Street Bar is a fantastic place to catch a game on TV and hang out with friends. They also have THE BEST crab cakes in Annapolis (ya, it is unexpected for us too). At night (after 1000pm) Dock Street Bar turns into a lively night club. Annapolis has no shortage of bars/clubs, but many of them are overrun with college-age students. Dock Street Bar is where the locals go.
12 locals recommend
Dock Street Bar & Grill
136 Dock StDock Street Bar is a fantastic place to catch a game on TV and hang out with friends. They also have THE BEST crab cakes in Annapolis (ya, it is unexpected for us too). At night (after 1000pm) Dock Street Bar turns into a lively night club. Annapolis has no shortage of bars/clubs, but many of them are overrun with college-age students. Dock Street Bar is where the locals go.
Shopping
Bookstore and Coffeehouse, this unique historic home has been converted into a cozy place to find a book, sit down, and read it cover-to-cover. Say hi to our friend Ginny (the owner) and she can help you find the perfect book!!
15 locals recommend
Old Fox Books & Coffeehouse
35 Maryland AveBookstore and Coffeehouse, this unique historic home has been converted into a cozy place to find a book, sit down, and read it cover-to-cover. Say hi to our friend Ginny (the owner) and she can help you find the perfect book!!
Stop in at any of the antique stores on Maryland Ave, but don't miss Evergreens. If you can catch her, say hi to our friend Joanna (the owner) and she can help you find anything.
Evergreen Antiques
69 Maryland AveStop in at any of the antique stores on Maryland Ave, but don't miss Evergreens. If you can catch her, say hi to our friend Joanna (the owner) and she can help you find anything.
Funky little shop with constantly new inventory. Stop in a say hi to our friend Lisa (the owner) and don't forget to pet little FJ.
Barefoot Dwelling
100 Maryland AveFunky little shop with constantly new inventory. Stop in a say hi to our friend Lisa (the owner) and don't forget to pet little FJ.
Arts & Culture
Annapolis Summer Garden Theatre
143 Compromise StThe Colonial Players
108 East StSightseeing
Hop onto one of the Schooner Sail boats and treat yourself to a tour of the Bay Bridge, Chesapeake Bay, Naval Academy Sites, and more. They have specialty beer/wine tasting trips as well as romantic sunset cruises. Check their website!
34 locals recommend
Schooner Woodwind Sailing Cruises
80 Compromise StHop onto one of the Schooner Sail boats and treat yourself to a tour of the Bay Bridge, Chesapeake Bay, Naval Academy Sites, and more. They have specialty beer/wine tasting trips as well as romantic sunset cruises. Check their website!
Take the Annapolis Water Taxi, a Dinner Cruise, or a half-day trip to St. Michael's. Call ahead for details or stop into their West Street office for more brochures adventure opportunities.
CALL THE WATER TAXI: 410-263-0033 OR VHF 68
32 locals recommend
Watermark Tours, Charters, Cruises
1 Dock StTake the Annapolis Water Taxi, a Dinner Cruise, or a half-day trip to St. Michael's. Call ahead for details or stop into their West Street office for more brochures adventure opportunities.
CALL THE WATER TAXI: 410-263-0033 OR VHF 68
Don't pay for other Annapolis/USNA Tours. The USNA Visitor's Center offers free tours daily. Checkout their website for details!
https://www.usnabsd.com/for-visitors/public-tours/
13 locals recommend
Armel-Leftwich Visitor Center
52 King George StDon't pay for other Annapolis/USNA Tours. The USNA Visitor's Center offers free tours daily. Checkout their website for details!
https://www.usnabsd.com/for-visitors/public-tours/
Free self-guided tours!
Stop into the State House and learn about the oldest U.S. state capitol in continuous legislative use. Walk through the same halls as President Washington, Mr. Paca, Mr. Lafayette, Mr. Tilghmanand other historic figures of country's history. View up close the largest wooden dome in the United States constructed without nails and learn how the lightning rod at the top--designed by Benjamin Franklin--has kept it safe for so many years.
81 locals recommend
Maryland State House
100 State CirFree self-guided tours!
Stop into the State House and learn about the oldest U.S. state capitol in continuous legislative use. Walk through the same halls as President Washington, Mr. Paca, Mr. Lafayette, Mr. Tilghmanand other historic figures of country's history. View up close the largest wooden dome in the United States constructed without nails and learn how the lightning rod at the top--designed by Benjamin Franklin--has kept it safe for so many years.
Historic Annapolis Museum Store
77 Main StVisit the five-part Georgian mansion William Paca House and gardens built in early 1760s. Beautifully restored by Historic Annapolis, this is gimps into our nation's history.
186 Prince George St
186 Prince George StreetVisit the five-part Georgian mansion William Paca House and gardens built in early 1760s. Beautifully restored by Historic Annapolis, this is gimps into our nation's history.
Walk into 18th century Annapolis's Hogshead to learn what life was like for the “lower and middling sort” in early Maryland post Revolutionary War. Hear from expert guides dressed in period attire.
43 Pinkney St
43 Pinkney StreetWalk into 18th century Annapolis's Hogshead to learn what life was like for the “lower and middling sort” in early Maryland post Revolutionary War. Hear from expert guides dressed in period attire.
Hammond-Harwood House
19 Maryland Ave