If you’re looking for the flipside of Annapolis proper, take the water taxi from the City Dock or cross the Spa Creek Bridge near the Annapolis Waterfront Hotel to explore the colorful community of Eastport. A peninsula bounded by Back Creek, Spa Creek and the Severn River, it is home to a bevy of restaurants, each with its own individual personalities and all of them pleasant.

Blackwall Hitch (named after a British nautical knot) is a lighthearted upscale restaurant whose charms extend from a wine and oyster bar, a communal dining table and a roof-top deck. Seafood is a specialty in the handsome dining room and a lavish Sunday brunch is popular with locals. A robust bar scene attracts an urban chic crowd who come to mingle and for live music Wed–Sun nights. Lunch and dinner. 400 6th St., 410-263-3454.

Boatyard Bar & Grill owner and former Wall Streeter Dick Franyo has high standards for the fare featured at this sailing-themed establishment where the atmosphere is casual, service is super, kids are welcome (especially in the rear dining room) and the long bar serves as a popular place for socializing. Early birds love the traditional breakfasts (homemade muffins included), there is an outdoor deck where pets are welcome, lobster rolls are a Saturday special, and the menu ranges from pizza to Eastern Shore-inspired entrees. I love to take out-of-towners here for a reliably positive exposure to “the other Annapolis.” 400 4th St, breakfast/lunch/dinner. 310-216-6206.

Carrol’s Creek is a must-stop for visitors seeking a close-up of berthed boats, a view of the Naval Academy on the opposite shore, deck dining, consistently excellent food and wine, professional service, a handsome inside dining room and the town’s best bar happy hour (half-price entrees). Owned and operated by the Jacobs family, this is one of the premier restaurants in Annapolis. Sample the lobster bisque, all-lump crab cakes, sauced scallops nestled under strips of phyllo and a variety of beef entrees. 410 Severn Ave. 410-263-8102.

Chart House, Annapolis version, claims a stunning location on the site of Trumpy’s boatyard. It was here that the finest crafts in the world were built, including boats used in World War II. Access is via a dock running alongside the handsome restaurant, where luxury personal and corporate boats are moored. A sumptuous salad bar occupies a place of honor in the rear of the dining room, where diners feast on seafood and other regional specialties. The bar area overlooks the water and is a fine vantage point for watching the Anapolis Yacht Club’s Wednesday night races. Open daily for dinner 4:30 p.m. – 9:00 pm. Sunday brunch. 300 2nd Ave. 410-268-7166.

The tagline for Davis’ Pub, “Where there are no strangers. Just friends you haven’t met yet”, is fitting for this delightful dive, so “real” it was featured on the Food Network’s Diners and Dives. Its welcome extends to well-behaved dogs on the popular sidewalk patio. The inside is pretty dim, the better to watch sporting events on the flat screen TVs above the bar. Opened in 1920 by a fellow named George Washington Davis, the establishment has evolved from a general store to a popular neighborhood pub serving golf-ball size crab balls, crab pretzels, good burgers, daily lunch specials and a dinner menu till 11 pm, when light fare takes over. Chester Ave and 4th St. 410-268-7432. Open 11 am–2 am.

There are those who consider family-owned Lewnes’ Steakhouse several cuts above other beef-centric establishments. The Lewnes family has been in the food business since 1921, owning a series of eateries in Annapolis. The steakhouse, open since 1989, is named after Sam Lewnes, the patriarch of the clan and its current owner. The restaurant’s clubby atmosphere encourages loyalty to a menu where patrons may choose the size of their filets and share side dishes of starch and veggies. The steaks are legendary (the filet is baseball-size) as are the lamb chops, veal chop, black bean soup, signature Greek salad and an awesome house-made pecan pie. Be aware that this is a pricey place – but worth the outlay. Dinner only. 410-263-1617.

Housed in a restored cottage on the old Trumpy Boatyard, O’Leary’s Seafood Restaurant is considered by some to be the finest seafood restaurant in Annapolis. The chef gets a daily delivery of sustainable fish, preparing them in a variety of styles. You could make a memorable meal by choosing several of the appealing appetizers (grilled scallops paired with lumps of Maryland crab, lettuce wraps with grouper, Prince Edward Isle mussels) or go for the house favorite entrée of fried local rockfish. Service is thoughtful; the wine list, savvy. Framed artwork is by Wil Andersen. Dinner 5–9 pm. 310 3rd Ave. 410-263-0884.

At the Annapolis location of Ruth’s Chris, a replica of the red-roofed Thomas Point Lighthouse perches atop this famous steakhouse. Owned and operated by a local restaurateur, it possesses a gorgeous outdoor dining patio on the ground floor, adjacent to an attractive bar area that includes booth seating. Here, you will find a bargain bar menu during happy hour, when artisan cocktails are $7, a super burger is $12 and a filet mignon sandwich is $16. Best-quality steaks, lamb chops, Maine lobster and veal are on the a la carte menu and service is faultless. Lounge opens daily at 4 pm, dinner Sun 4–9 pm, Mon–Thurs 5–10, Fri-Sat ‘till 11 pm.

For more restaurant suggestions across Annapolis & Anne Arundel County, along with things to do and upcoming events,  check out VisitAnnapolis.org.


Photos courtesy of VisitAnnapolis.org and John Bildahl