Chessie’s Wharf: A New Favorite Hangout in Annapolis with a Twist
There’s something special about reconnecting with old friends after months (or years) apart. For me, Chessie’s Wharf in West Annapolis was the perfect setting for such a reunion. Nestled at 609 Melvin Avenue, this new spot by RAR Brewing might not be on an actual wharf—despite its name—but it certainly serves up a memorable experience, blending great craft beer, good food, a crush flight and some hearty laughs.
Not Quite a Wharf, but Still Worth the Trip
I planned to meet a group of friends there, each of us coming from different corners of Maryland: Crownsville, Howard County, and right here in Annapolis. As we circled the block, all of us had a good chuckle over the fact that Chessie’s Wharf isn’t on a wharf at all. Situated in West Annapolis, the taproom occupies the building that once housed the Mexican Café. So, if you’re expecting waterfront views, well, adjust those expectations—but trust me, you’re in for a treat anyway!
The Vibe: Casual, Nautical Fun
Once inside, we were greeted by a quirky, nautical theme that made us all smile. The legend of Chessie, the mythical Chesapeake Bay sea monster, is alive and well here. Tap handles are shaped like the creature, and walls are decorated with Big Mouth Billy Bass plaques that occasionally burst into sea shanties or ’90s anthems. It’s the kind of place that doesn’t take itself too seriously, which was exactly what we needed for a long overdue catch-up session(RaR Brewing)(Craft Beer Times).
Brews & Bites: A Menu That Delivers
We kicked things off with a round of RAR Brewing’s signature beers. With 28 taps pouring everything from their popular Nanticoke Nectar IPA to more experimental sours like the Creamsicle Colored Sour, there’s a flavor for every palate. I opted for the Out of Order Sour, while a couple of my friends couldn’t resist trying the Chessie Deluxe Burger—double patties, cheese, and all the fixings. It was the perfect comfort food for a night filled with reminiscing and belly laughs(RaR Brewing)(Center Maryland).
The menu here is simple but packed with flavor. Beyond the burgers, the Pool Hall Dog—a playful nod to RAR Brewing’s beginnings in Cambridge—was another hit at our table. We also perused the cans to-go as souvenirs, promising to save them for our next reunion (although I’m not sure they lasted the week)(Brew Scoop).
Laughter, Confusion, and Good Times
Despite the initial confusion about the “wharf” that wasn’t, our time at Chessie’s Wharf was nothing short of fantastic. Between the nostalgic tunes from the fish plaques and making fun of UConn, we laughed harder than we had in a long time. The friendly staff and relaxed vibe made it easy to just enjoy the moment.
Pro Tip: If you’re meeting a group, get there early. The place gets busy, especially on weekends, and the outdoor seating is perfect when the weather’s nice. Oh, and don’t forget to try the rotating guest taps—there’s always something new to explore(West Annapolis Business Association).
Chessie’s Wharf Details
609 Melvin Ave, Annapolis, MD 21401
Hours: Mon–Thu 11 AM–9 PM, Fri–Sat 11 AM–11 PM, Sun 11 AM–9 PM
Check them out on Instagram: @chessieswharf
Now that I have you convinced that you want to be able to walk to this spot from the comfort of your own home…get your house hunt on at the button below. A curated collection of properties that put you right in and around West Annapolis
