Date nights, family meals, catching up with friends — what do they all have in common? Restaurants. We love to gather over a good meal, whether we’re getting to know someone new, reconnecting with loved ones or simply taking a break from cooking. And while dining out is always a treat, there’s something especially magical about enjoying dinner outside on a summer evening.
Date nights, family meals, catching up with friends — what do they all have in common? Restaurants. We love to gather over a good meal, whether we’re getting to know someone new, reconnecting with loved ones or simply taking a break from cooking. And while dining out is always a treat, there’s something especially magical about enjoying dinner outside on a summer evening. That’s where Dinner Under the Stars comes in.
Hosted by the Inner West Street Association, this Annapolis tradition runs every Wednesday night from May 20 to September 30, from 5 to 10 p.m., with a few special Saturday evenings throughout the season. Live music adds to the atmosphere from 6 to 9 p.m. Not dining? You can still bring a lawn chair, stroll through the area and enjoy the music and energy of the evening.
Here are the seven participating restaurants.
49 West
Inspired by European coffeehouses, 49 West aims to bring the community together through art, music and food. The menu includes a wide variety of handhelds, appetizers, soups and salads, along with two quiche options served all day.
El Toro Bravo
Curating homemade Mexican dishes, El Toro Bravo prides itself on fresh ingredients, never frozen or canned items. The made-to-order menu offers something for everyone, from guacamole, dips and wings to house specials, quesadillas, fajitas, burritos, seafood dishes and a children’s menu.
Luna Blue Ristorante
Regarded as one of the best Italian spots in Annapolis, Luna Blu has been serving the community for more than two decades with a warm, intimate and inviting dining experience. The menu features Italian classics such as mozzarella caprese and penne alla vodka, along with Maryland-inspired options like crab bruschetta and salmone con spinaci. One popular option is the four-course dinner special, a fixed-price meal that includes an appetizer, house salad, entrée and dessert.
Picante Annapolis
This family-owned restaurant brings classic Mexican dishes with a Oaxacan twist to Annapolis. Picante’s menu includes house specialties, fajitas, tacos, soups and more. One standout option is the asada fries: french fries topped with cheese, carne asada, pico de gallo, sour cream and guacamole.
Rams Head Tavern
If you’ve lived in Annapolis for more than a week, chances are you’ve heard of Rams Head. A community staple since 1989, Rams Head Tavern is known for music and nightlife, hosting more than 300 concerts each year. The menu includes seafood favorites such as Chesapeake deviled eggs, crabby tots, crab dip, cream of crab soup, fish tacos and crab cakes. Not a seafood lover? There are plenty of other options, including burgers, mac and cheese, a vegan chorizo bowl, steak frites, chicken dishes, tacos, salads and wings.
Stan and Joe’s Saloon
Celebrating its 18th year as a community vendor, Stan and Joe’s offers casual favorites such as nachos, mozzarella sticks, wings, onion rings and fries. Guests can also try signature stogies, a chicken salad croissant sandwich or one of the rotating daily and weekly specials.
Tsu
Formerly known as Tsunami Sushi Bar and Lounge, Tsu is a go-to destination for sushi in Annapolis. The menu includes sushi rolls, sashimi and nigiri, starters, shareable platters, rice bowls and noodle bowls, with a handcrafted menu centered on seafood and the flavors of the ocean.
More to Enjoy Beyond Dinner
Dinner Under the Stars is about more than great food. Each week, West Street comes alive with live music, dancing, games and local arts experiences. Guests can enjoy performances ranging from big band and Motown to salsa, jazz, local bands and Frank Sinatra tributes. Line dance lessons with Dean Garrish are also offered on select Wednesdays throughout the season.
Looking for something more active? Annapolis Pickleball Club hosts Pickleball Under the Stars every Wednesday at the top of West Street, outside Sadona Salon + Spa. Courts are marked from 5 PM until late, giving guests a chance to play before or after dinner.
Visitors can also explore local art galleries, learn to paint with Gallery 57 West on select evenings, take on a challenge at Mission Escape Room or check out new exhibits at The Annapolis Collection Gallery, Annapolis Pearl Gallery and Gallery 57 West.
Whether you come for dinner, music, dancing, pickleball or a stroll through the galleries, Dinner Under the Stars offers plenty of ways to enjoy a summer evening in Annapolis.
With great restaurants, live entertainment, local art and plenty of ways to spend the evening, Dinner Under the Stars is one of Annapolis’ signature summer traditions. Whether you’re planning a date night, meeting friends or bringing the family downtown, it’s a chance to enjoy West Street at its best. Outdoor seating is limited, so reservations are strongly recommended.
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