The restaurant hours and menu selections are subject to change.  We do our best to keep the information updated and current.  We recommend calling ahead on weekends.

Walking from High Street Landing up Historic High Street to the local restaurants, you will be walking through history.  Portsmouth gets its name from the English naval port of Portsmouth, England. The town was laid out checkerboard style with 122 half-acre lots around its town square at High and Court streets. Streets were organized in a grid pattern with street widths alternating between 32, 50 and 100 feet. Each block or square was named for noted Virginians, Englishmen, or places in England or the United States.  Streets were named similarly.

High Street was named for the main commercial corridor in Portsmouth, England. It is 100 feet wide, with two narrow parallel streets of 32-foot widths (Queen and King streets), located to the north and south. Narrower streets served as alleys for High Street, facilitating the access to commercial buildings from the rear. 

Enjoy your walk to the following restaurants:

Market Square - 300 Block                                                                                                  Bounded by Middle, King, Court and High Streets.  In 1752 when Colonel William Crawford established the town of Portsmouth he designated part of this square for a market, hence the name, although a market was never erected at this location.

China Garden
Chinese and Asian Cuisine
301 High Street. 757.399.8888
Features a 40-item all-you-can-eat lunch and dinner buffet, plus menu items and daily specials.

Hours:

Café Europa
French and Italian Cuisine
319 High Street. 757.399.6652
Offers Mediterranean cuisine in an elegant dining atmosphere. Seafood, chicken, veal pasta Reservations suggested. Serving Lunch & Dinner. Outside Café Dining.

Hours: Tuesday thru Friday 11:30 a.m. to 2 p.m. Tuesday thru Thursday 5 p.m. to 9:30 p.m.; Friday and Saturday 5 p.m. to 10 p.m.

Lobscouser
American, Seafood, Steaks Cuisine
337 High Street. 757.397.2728
Small, informal restaurant specializing in seafood. Ask about the daily lunch specials and arrive between 5 and 6:30 p.m. for the early bird dinner specials. Serving Lunch & Dinner.

Hours: Monday thru Friday 11:30 a.m. to 2 p.m.; Monday thru Thursday 5 p.m. to 9 p.m.; Friday and Saturday 5 p.m. to 10 p.m.

New York Deli
Deli, American Cuisine
509 Court Street. 757.399.3354
A Portsmouth landmark for 57 years. Bagels, homemade soups, traditional hot and cold deli fare and desserts. Serving breakfast and lunch. Smoking and non-smoking sections, Handicapped access, No credit cards. Outside Café Dining.

Hours: Monday thru Saturday 8 a.m. to 4 p.m. Sunday closed.

Courthouse Square - 300 Block
Bounded by Middle, High, Court and Queen Streets. Crawford designated part of this same square for the erection of a court house, hence the name Courthouse Square.

Roger Brown’s Restaurant & Sports Bar
Pizza, Seafood and American Cuisine
316 High Street. 757.399.5377
Neighborhood: Olde Towne
This NFL legend's ultimate sports bar features cafe and casual dining with traditional American dishes. Also enjoy a 50-seat bar, pool tables, a video arcade, theater seating, multiple TVs with satellite feed, and three big-screen TVs. Serving Lunch & Dinner. Outside Café Dining. Entertainment Schedule.  www.rogerbrowns.com

Hours: Daily 11 a.m. to Midnight; Friday and Saturday 11 a.m. to 2 a.m.

Brutti’s
Bistro, Coffee House, Seafood and American Cuisine
467 Court Street. 757.393.1923
This European bistro and restaurant serves an eclectic menu, certified angus beef, steaks, chops, seafood, pasta, wood stone oven, European-American specialties. Full top shelf bar, creative martinis and specialty wine list. Wild and wonderful desserts. Brutti's is known for its overstuffed omelets for brunch, French toast, and pastries in the morning. Local favorite includes the BagelNutz - a soft puff of bagel dough with cream cheese baked inside. Parisian style sandwiches and salads are offered for lunch. Reservations suggested. 2003 & 2004 Wine Spectator Award. Serving Breakfast, Lunch, Dinner & Sunday Brunch. Outside Café Dining. Entertainment Schedule. www.bruttis.com

Court Street Cordials
American, Desserts
455 Court Street. 757.399.6400
Features a selection of cheese and dessert fondue including "Pink Champagne & Cream" and "Brandy Chocolate" fondues. Also features a variety of entrees including Surf & Turf, Filet Mignon and "Olde Towne Trio" (shrimp, marinated sirloin and chicken). Desserts are prepared fresh each day by a pastry chef. Cordials' offers a variety of dessert wines, sherry's, ports and recommended red wines to enhance the dessert experience.

Hours:

Church Square - 400 Block
Bounded by Court, King, Dinwiddie and High Streets. When William Crawford, founder of Portsmouth, laid out the street plan in 1752, he designated the intersection of High Street and Court Street as the town center and set aside space for a parish church. In 1761, when the Vestry of Trinity Church was formed with Crawford as a member, the original church building comprised most of what is now the nave.

Commodore Theatre
American Cuisine
421 High Street. 757.393.6962
A luxuriously restored 1945 Art Deco-style motion picture theater serving light American fare daily. Enjoy a meal with an afternoon or evening movie. Menu includes appetizers, sandwiches, light fare and desserts. Full bar available. Our unique ordering system allows you to pick up the phone on your table and place your order directly to our kitchen (your order must be placed before show starts). Cash only is accepted at the box office. Credit & debit cards are accepted in the dining area only. Call for theatre & show information. www.commodoretheatre.com.

Hours:

Prison Square - 400 Block
Bounded by Court, High, Dinwiddie, and Queen Streets. It was so named because Crawford in 1752 had designed part of this square for the erection of a prison.

Oxford Square - 500 Block
Bounded by Dinwiddie, High, Washington and Queen Streets.  Named after the well known street in London, England.

The Baron’s Pub
Pub Fare, American Cuisine
500 High Street. 757.399.4840
This neighborhood pub is famous for its "Baron Burger," made with ½-pound of lean ground beef, sautéed onions and mushrooms, lettuce, tomato, and melted American and provolone cheeses. Pub favorites include oyster sandwich, classic Reuben and Cajun chicken sandwiches. Choose from a variety of nine different pizzas. The "After Five Menu" features surf & turf, steaks and a scallop platter. Serving Lunch, Dinner & Late Night. Outside Café Dining. Entertainment Schedule. www.baronspub.com

Hours: Monday thru Saturday 11 a.m. to 2 a.m., Sunday 12 p.m. to 2 a.m. Live Entertainment Thursday thru Saturday 9 p.m. to 2 p.m.

Cheshire Square - 600 Block
Bounded by Washington, King, Green and High Streets. It was probably named for the English County of Cheshire.

Chez Papillote
French
623 High Street. 757.967.9494
A French-themed catering hall, inspired by the catering halls that served as the cornerstones of the Brooklyn neighborhood where owner David Golay lived while attending the French Culinary Institute in New York. Chez Papillote will also serve lunch during the week and host wine-tasting dinners and other special events. www.chezpapillote.com.

Hours:

Devonshire Square - 600 Block
Bounded by Washington, High, Green and Queen Streets. Named after the English County of Devonshire.

Amore'
Casual Italian Food
606 High Street. 757.337.8382
A family-friendly, casual restaurant serving Italian cuisine, such as homemade meatballs, pizza, subs, spaghetti and lasagna. Serving Breakfast, Lunch, Dinner & Sunday Brunch.

Hours:

Montgomery Square - 700 Block
Bounded by Green, King, Effingham and High Streets.  It may have been named after Robert Montgomery (1736-1775), brigadier general in Continental Army who was killed leading the assault on Quebec, or it may have been named after the Herbert family, hereditary Earls of Montgomery.

Comfort
Southern
725 High Street. 757.393.3322                                                                                             Neighborhood: Olde Towne
Portsmouth is the second location for this popular restaurant, the first of which was opened by Jason Alley five years ago in Richmond, Virginia.  Known for its "serious Southern cooking," Comfort specializes in country cooking, such as fried green tomatoes, meatloaf, creamed spinach, macaroni and cheese, cheddar cheese grits - all with a touch of flair - in a roomy, casual, hip atmosphere. www.comfortrestaurant.com

Hours:

Washington Square - 700 Block
Bounded by Green, High, Effingham and Queen Streets. It was named after George Washington (1732-1799), commander–in-chief of Virginia troops, 1775, and of all Continental troops, 1775, first President of the United States.

Gosport Marketplace & Deli
Deli
702 High Street
Neighborhood: Olde Towne                                                                                                              A storefront restaurant with a name inspired by the shipbuilding history of this quaint historic seaport city coming soon. The marketplace and deli are open now featuring Boars Head brand meats. www.gosportdeli.com.

Hours: Daily 11 a.m. to 6 p.m.

Bob's BBQ and Country Cooking
American, Barbeque Cuisine
417 County Street. 757.399.8060
Sliced, chopped and beef barbecue plates, fish dinners and country cooking. Serving Breakfast & Lunch.

Hours: Monday thru Friday 6:30 a.m. to 4 p.m.; Saturday 6:30 a.m. to 2 p.m.; Sunday closed.

Hours: Monday thru Thursday 11:30 a.m. to 2:30 p.m. and 5:30 p.m. to 10 p.m. Friday and Saturday 11:30 a.m. to 11 p.m. Sunday 11:30 a.m. to 9 p.m.

The Circle Restaurant
American
3010 High St. 757.397.8196
Recently renovated and reopened by its original owners, the Mathews family, The Circle Restaurant was recently placed on the Virginia Landmarks Register and the National Register of Historic Places. The Circle Restaurant was built as a curb-service restaurant in 1947. The building's modern style of design, its architectural integrity and its association with the rise of the automobile in American culture after World War II were all cited in the designation. The Circle features the first circular glass wall used in a building. It switched from a curb service drive-in to a regular restaurant format in the late 1960s. Today, The Circle continues its tradition of food, friendly service and reasonable prices. Features a daily lunch buffet and a breakfast buffet on Saturday and Sunday.

Hours:

The Deck Restaurant
Seafood, Steaks, American Cuisine
10 Crawford Parkway (at the Tidewater Yacht Marina). 757.398.1221
Neighborhood: Olde Towne
Selections range from king crab legs, steamed clams, oysters, mussels, and shrimp to chicken wings, fried calamari, fish bites, salads, soups, sandwiches, burgers, and chicken. Serving Lunch, Dinner & Late Night. Outside Waterfront Dining. www.deckrestaurant.com

Hours: Lunch served Tuesday thru Sunday 11 a.m. to 2 p.m.; Dinner served Monday thru Sunday 5 p.m. to 2 a.m.

Flagship Restaurant & Raw Bar
American
103 Constitution Avenue. 757.398.1600
The newly renovated Flagship Restaurant and Raw Bar, located in the Shea Terrace section of Portsmouth, offers casual dining with a neighborhood atmosphere. Appetizers range from crab balls and tuna bites to shrimp cocktail and chicken wings. The Flagship also offers a variety of soups, salads, sandwiches and wraps. The entrees range from fish and chips to prime rib dinners to pasta dishes like linguini with clam sauce. With a fun kid's menu and family atmosphere, you will love to bring the family out to eat. Amazing food, great service, daily lunch and dinner specials along with special events such as after work deck parties offering live music will make this the place you love to call your second home. Arrive by car or take advantage of the boat dock just outside. www.theflagshiprestaurant.com.

Hours: Open Daily 11:00 a.m. to 2:00 a.m. seven days a week.

Foggy Point Bar & Grill
Seafood, Steaks, American Cuisine
Renaissance Portsmouth Hotel, 425 Water Street. 757.673.3032
Olde Towne's waterfront landmark offers a varied menu elegantly prepared in a posh but casual setting. From the scenic waterfront river views, this restaurant features fresh seafood daily, with names like crab & corn soup, sautéed red snapper and grilled salmon. Lunch menu includes soups salads, sandwiches and a Signature crab cake sandwich. Serving Breakfast, Lunch, Dinner & Sunday Brunch. Outside Waterfront Dining. www.renaissanceportsmouth.com/dining

Hours: Daily; Breakfast Monday thru Friday 6:30 a.m. 11 a.m.; Lunch 11 a.m. to 2 p.m.; Dinner 6 p.m. to 10 p.m.; Sunday Brunch 11 a.m. to 2 p.m. Lunch, dinner, and late night food are served at the Foggy Point Bar.

Island Grill
Seafood, American Cuisine
Holiday Inn Olde-Towne, 8 Crawford Parkway. 757.393.2573
Located in the Holiday Inn-Olde Towne, the Island Grill offers a waterfront view and great atmosphere. Check out the lunch buffet Monday through Friday. Restaurant overlooks Elizabeth River and Norfolk skyline. Serving Breakfast, Lunch & Dinner. Outside Waterfront Dining. Entertainment Schedule. www.portsmouthva.holiday-inn.com/restaurant.asp

Hours: Daily - Breakfast 6:30 a.m. to 11 a.m.; Lunch 11 a.m. to 2 p.m.; Dinner 5:30 p.m. to 10 p.m.

La Tolteca
Authentic Mexican Cuisine
1 High Street. 757.391.2828
Features authentic Mexican cuisine. Serving Lunch & Dinner.

Hours Monday thru Saturday 11 a.m. to 10 p.m.; Sunday 12 p.m. to 9 p.m.

Logan Raye's Key West Grille
Seafood
Raw bar and pub. 606 Court St. 757-295-0946.

Hours:

Paddy O'Brian's Olde Towne Bar & Grill
American Cuisine
612 Court Street. 757.399.6120
Neighborhood: Olde Towne
Eight different burgers including a signature burger "The Big Daddy", a 1 lb. burger cooked your way! Gourmet Pizzas, Wraps, Buffalo Scallops, Steamed Shrimp, Blackened Scallops. Serving Lunch & Dinner. Outside Café Dining.

Hours: Daily 11 a.m. to 2 a.m.

Sun's Subs & Pub
Fast Food, American Cuisine
608 Court Street. 757.399.1356
Neighborhood: Olde Towne
Choose from a selection of hot and cold subs, pizza, hot dogs and sandwiches. Serving Lunch & Dinner.

Hours: Monday thru Saturday 10 a.m. to 9 p.m. Sunday closed.

Thumper's Olde Towne Cajun Grill
Cajun Cuisine
600 Court Street. 757.399.1001
Neighborhood: Olde Towne
Features Cajun food, such as Fried Gator Bites, Blue Crab Stuffed Mushrooms, Burgers, Sandwiches, Bourbon St. Blue Steak, Cajun Fried Stuffed Shrimp, Crawfish or Shrimp Etouffee over rice. Serving Lunch & Dinner. Outside Café Dining.

Hours: Monday thru Saturday 11 a.m. to 2 p.m.; Sunday 4 p.m. til.