Annapolis Social

Let’s get together for a Tuesday night happy hour at one of Annapolis’s most beloved gathering spots. The BoatYard Bar & Grill is a local institution—founded with the spirit of Eastport’s maritime history and sailing community, it’s become a go-to for sailors, locals, and visitors alike. The vibe is casual, lively, and steeped in the neighborhood’s boatyard heritage.
What to expect
• Happy hour specials at the bar with a wide selection of drinks
• Highly recommended mussels on the happy hour menu—fresh, flavorful, and a local favorite
• Don’t miss their classic coddies, a Maryland tradition that pairs perfectly with a cold beer
• Good company and a chance to enjoy the warm, welcoming Eastport atmosphere
Plan
• Arrive anytime after 5:00 pm; we’ll gather at the bar area
• Order what you like from the happy hour menu; everyone settles up individually
• Casual, come as you are
Good to know
• Parking (free street parking) is available nearby on the street, you may have to circle around a time or two but you'll find something within 3 blocks
• The BoatYard can get busy, so arriving early helps grab a good spot
RSVP
Please RSVP so we can look out for you. It’s the perfect way to enjoy Eastport’s food culture midweek with new and familiar faces!

Join us for one of Annapolis’s favorite traditions — the Eastport Oyster Boys (Park Campus, 7300 Edgewood Rd in Eastport). These Thursday evening concerts have been bringing locals together for years: great music by the water, food trucks serving up delicious bites, drinks for purchase, and that laid-back Eastport vibe that makes this community so special.
This week’s headliner is the Eastport Oyster Boys, Annapolis’s own legendary “good-time” band. Known for their blend of island rhythms, maritime tunes, and tongue-in-cheek storytelling, the Oyster Boys have been called the voice of the Chesapeake. Their music celebrates the Bay, the boating life, and the characters that make this region unique. One of the band’s members, Kevin Brooks, even penned a book about Annapolis, adding to their deep roots in the community. Expect witty lyrics, sing-along choruses, and a performance that captures the heart and humor of Eastport.
Details:

• 🎵 Music runs from 6:00–8:00 PM
• 🪑 Bring a chair or blanket to settle in comfortably
• 🍔 Food trucks on site and drinks (beer, wine, cocktails) available for purchase
• 🚫 No outside alcohol permitted inside the venue
• 💵 Admission supports the Maritime Museum and its programs

This is one of those nights that feels like pure Annapolis — music by the water, neighbors and friends gathered, and the Eastport Oyster Boys setting the tone. Don’t miss it!
Important:

• RSVP is required for planning and any attendee participation.
• Events with fewer than 4 signups are subject to cancellation—please check RSVPs on the day of the event.

Wednesday nights are for good food, good wine, and good friends. Join us at Blackwall Hitch, a landmark in Eastport that blends modern coastal dining with the history and charm of Annapolis’s maritime roots. From its brick-and-beam character to the waterfront setting, this is one of those places where you feel connected to the city’s story while enjoying a warm, lively atmosphere.
Every Wednesday, pasta is ½ price all day, and bottles of wine are half off too. Happy hour runs until 6pm if you’d like to come early, but the pasta and wine special is available all evening. Free parking is available in Blackwall’s private lot, making it an easy night out.
We’ll keep this standing tradition going (most weeks) through the Fall and Winter, giving us all something delicious and social to look forward to midweek.
Important:

• RSVP is required for planning and table reservations.
• Events with fewer than 4 signups are subject to cancellation—please check RSVPs on the day of the event.

Come hungry, come curious, and come ready to enjoy a Wednesday night classic with Annapolis Social!

Join us for an easy, social happy hour right on the Eastport side of Spa Creek. Chart House sits on a prime stretch of waterfront where shipbuilding once defined the neighborhood—today Eastport is a lively, walkable peninsula with marina views, local history, and a laid-back vibe that’s perfect for a midweek meetup.
What to expect
• Great drink specials and happy-hour bites at the bar
• A chance to sample their delicious seafood and apps without committing to a full dinner
• Friendly company and postcard views of the harbor, bridges, and sailboats drifting by
Plan
• Arrive anytime after 4:30 pm; we’ll gather at the bar area (Happy Hour pricing ends at 6)
• Look for the group near the high-tops; we’ll keep a couple of seats open as folks arrive
• Casual attire; come as you are after work or errands
Good to know
• Street parking in Eastport is typically free within a block or two in the evening
• Menu and specials vary—order what you like and settle up individually

Please RSVP so we can plan for headcount. If plans change, update your RSVP so someone else can take your spot. Can’t wait to toast a beautiful October evening together!