49 West Coffeehouse, Winebar & Gallery

Just 35 minutes from Chesapeake Paradise, 49 West Coffeehouse, Winebar & Gallery in Annapolis offers fresh, simple dishes, desserts, and breakfasts in a cozy, artistic atmosphere. A local favorite for live music on weekends and Sunday afternoons, it’s a perfect blend of charm, culture, and comfort.

Located at 49 West Street, Annapolis, MD 21401, 49 West Coffeehouse, Winebar & Gallery is a beloved local gem and one of Shawn Mahshie’s personal favorite Annapolis spots. Tucked just past the top of the main tourist street, this café and wine bar offers a cozy retreat filled with art, music, and great food.

Guests can enjoy fresh, simple dishes, homemade desserts, and delicious breakfasts, all served in a warm, European-style setting. The menu features locally roasted coffee, light lunches, small plates, and a well-curated wine selection. In the evenings, the space transforms into an intimate music venue with live performances on weekends and sometimes Sunday afternoons, offering everything from jazz to acoustic sets.

The rotating art exhibits, friendly staff, and creative atmosphere make 49 West a true reflection of Annapolis’s local charm—an ideal stop before heading back to relax by the water at Chesapeake Paradise.

For hours or event listings, call (410) 626-9796 or visit in downtown Annapolis.