Best Restaurants for Outdoor Dining in Parole

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Regions

BaltimoreBaltimore SuburbsDistrict of ColumbiaEastern ShoreGreater AnnapolisMaryland - DC Suburbs

Neighborhoods

AnnapolisBowleys QuartersBuzzard PointCapitol HillCharles VillageColumbia

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Award-winning

MICHELIN

Accessibility

Wheelchair access

56 restaurants available nearby

How are Featured results ranked

A photo of Augie’s Mussel House & Sports Bar restaurant

1. Augie’s Mussel House & Sports Bar

4.1

Excellent(59)

$$$$

• Sports Bar • Annapolis

Booked 4 times today

Located at Annapolis Town Center, Augie's Mussel House & Sports Bar is the area's go-to spot for game day and beyond. Dig into Belgian-inspired mussels and clams alongside sports bar favorites in a lively atmosphere built for fun — high top seating throughout, wall-to-wall screens, a private lounge for game viewing, a covered patio, and several dart boards for friendly competition. Reserve your table and come see what everyone's talking about.

A photo of Blackwall Hitch - Annapolis restaurant

2. Blackwall Hitch - Annapolis

4.4

Awesome(2629)

$$$$

• American • Annapolis

Booked 28 times today

We can't wait for you to dine with us at Blackwall Hitch Annapolis! A dining experience blending the area’s finest in tastes & talents, Blackwall Hitch is a coastally inspired concept that creates a local connection. Here you’ll find seasonally driven and locally sourced food and spirits, great local music and the area’s friendliest staff and patrons. With each visit as you take in the local flavor, we guarantee you’ll be hooked in no time. Get hooked on the flavor.

A photo of Luna Blu - Annapolis restaurant

3. Luna Blu - Annapolis

4.9

Exceptional(2660)

$$$$

• Italian • Annapolis

Booked 14 times today

We opened in 2001 on the new up & coming hot spot of Inner West Street. We have grown into a neighborhood favorite among locals & tourists. Our cozy dining room with murals of the Amafi Coast is the perfect place for a date night or for making memories with friends & family. Offering innovative Italian fare prepared with a personal touch & the freshest local ingredients. Menu items are prepared fresh to order, which allows us to be very accommodating to food allergies. Many options for vegans, pescatarians, and gluten-free diners.Wednesday & Saturday from May - Sept on West Street's 1st block, we hold Dinner Under the Stars. All of the restaurants put tables & chairs under a light canopy, there is live music and dancing. We offer a 4-course special nightly, 1/2 priced bottles of wine every Wednesday, Pizza & Wine pairing Tuesday & Thursday nights & and bi-weekly wine dinners.View our events & specials www.lunabluofannapolis.com Thanks for supporting local business!

A photo of Positano Ristorante - Annapolis restaurant

4. Positano Ristorante - Annapolis

4.3

Awesome(163)

$$$$

• Italian • Annapolis

Booked 44 times today

Handcrafted pasta and wood-fired pizza and the warm hospitality of Italy to your neighborhood. Fresh ingredients. Classic recipes

A photo of Yellowfin Steak and Fish House restaurant

5. Yellowfin Steak and Fish House

4.2

Awesome(244)

$$$$

• Seafood • Davidsonville

Booked 1 time today

Yellowfin features a bright, contemporary design, sunset views on the scenic South River, exceptional service and award-winning food. Voted Annapolis' Best Happy Hour 15 years in a row! Serving 7 species of fresh fish, hard carved steaks, pastas, full sushi menu and an assortment of fresh seafood entrees. Yellowfin also serves lunch and an All You Can Eat Sunday Brunch Buffet every Saturday and Sunday starting. Yellowfin specializes in serving parties of any size in our dining room and up to 200 in our lower level banquet facility. Our private, waterfront banquet facility is the perfect place for wedding receptions, business meetings, baby showers and class reunions. Yellowfin is one of Maryland's premier dinning destinations and famous for it's sunsets.

6. Iron Rooster

4.5

Awesome(997)

$$$$

• Breakfast • Annapolis

Booked 11 times today

Whether you're looking for breakfast all day, lunch, supper or drinks, at Iron Rooster you'll find a new twist on traditional comfort food, legendary hospitality, and a real sense of community. Join us every day for breakfast, lunch, supper and late-night drinks. Whenever you're here, you'll enjoy delicious food, a cold drink, and an extra helping of hospitality.

A photo of Rams Head Tavern - Annapolis restaurant

7. Rams Head Tavern - Annapolis

4.7

Exceptional(1841)

$$$$

• American • Annapolis

Booked 21 times today

For over 30 years, Rams Head has been an award-winning favorite serving creative tavern fare. Rams Head offers an outstanding happy hour, a legendary beer selection, and extraordinary live music 7 nights a week. Whether in one of the cozy dining rooms, the historic pub, or on the Wisteria-covered patio, you'll see why so many Annapolitans consider Rams Head their second home. .We do not accept reservations for outdoor dining. Have tickets to a show at Rams Head On Stage? If taking advantage of our FREE Premium On Stage Experience, please make note in the 'special request' section while making your reservation.

8. Reynolds Tavern

4.4

Awesome(565)

$$$$

• Continental • Edgewater

Reynolds Tavern is a historic Annapolis destination offering Afternoon Tea, Fine Dining, and the 1747 Pub experience in one of the oldest tavern buildings in the U.S.Located on Church Circle in the Historic District, steps from shops, restaurants, and the U.S. Naval Academy, Reynolds Tavern blends 18th-century Georgian architecture with elegant, restored interiors.Guests enjoy English Afternoon Tea daily 11am–5pm, refined Fine Dining from 5:30pm, and casual fare in the 1747 Pub, celebrating the working tavern spirit. Guest-favorite signature dishes features Pasta Lafayette, Shrimp and Scallops, English comfort food Shepards Pie, fish and chips and everyone favorite bangers and mash, and locally sourced seafood, all house-made by our Executive Chef.Outdoor dining includes an elegant Upper Terrace and casual shaded Courtyard. Seating is first-come, first-served and weather permitting.Reynolds Tavern offers a timeless Annapolis dining experience for locals and visitors alike.

9. Zaytinya - DC

4.7

Exceptional(20384)

$$$$

• Mediterranean • Penn Quarter

Booked 280 times today

Under the direction of celebrated Chef José Andrés and his ThinkFoodGroup team, Zaytinya offers an innovative mezze menu inspired by Turkish, Greek and Lebanese cuisines served up in a sleek and modern setting. Building on José's deep knowledge of Mediterranean cooking and years of research and travel, the menu features shared small plates of authentic and innovative fare, creative cocktails, and unique Mediterranean wines, making Zaytinya one of the most exciting restaurants in Washington.

10. Bygone

4.7

Exceptional(4122)

$$$$

• American • Harbor East

Booked 22 times today

A fusion of the old, the new and the best of Baltimore. We’re an American gastro bistro that represents historic, vibrant, authentic Baltimore. We blend modern energy with a classic feel, celebrating luxury, excitement & an elevated dining experience. Plus, we’ve got some unbeatable views of our beautiful city!Bygone’s warm & welcoming atmosphere is reminiscent of an old-school social club, while our open rotisserie grill, whiskey bar & craft cocktails add a flair that is contemporary.Please note: No shows and cancellations made within less than 24 hours will be subject to a $75/per person fee.

See what locals rave about

From verified diners like you

L
LenaGold
Houston •6 reviews
5.0
Dined 2 days ago
Always superb!!! Erin (the owner) is the absolute best! Food is 100/10. Consistently superb.
More info
Luna Blu - Annapolis$$$$• Italian• Annapolis
•
4.9
H
Helen
Phoenix / Arizona •1 review
5.0
Dined 4 days ago
Delicious clams, Mussels and crab soup! Good prices. Highly recommend this place. We ate on the patio and it was lovely. Service was outstanding.
More info
Augie’s Mussel House & Sports Bar$$$$• Sports Bar• Annapolis
•
4.1
L
Lauren
Philadelphia County •4 reviews
5.0
Dined 5 days ago
We had an absolutely wonderful time at Positano’s! All of our food was delicious, and it is now our new favorite restaurant!
More info
Positano Ristorante - Annapolis$$$$• Italian• Annapolis
•
4.3
L
Linda
Baltimore / Maryland •8 reviews
5.0
Dined on May 24, 2026
Very good food, service and band!!! Fun crowd. Will be back
More info
Blackwall Hitch - Annapolis$$$$• American• Annapolis
•
4.4
T
Tori
1 review
4.0
Dined on May 16, 2026
We had a new server, but she was delightful and everything came out quickly and correct. I appreciated her honesty with being new and she was so kind. We had a table inside with a beautiful view, and I was very satisfied with the food. The prices were reasonable, and they had a nice variety of options. We got espresso and chocolate martinis and they were delicious! It’s a great date night spot or for a girls dinner. I think it would make a nice place for a special occasion, such as a graduation party of bridal shower given the view and the space they had. There was really nice ambience in the restaurant. I’m sure we will return!
More info
Yellowfin Steak and Fish House$$$$• Seafood• Davidsonville
•
4.2

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