2026 Cafe Diem: Annapolis Coffee Crawl
Expiration: Oct 4th 2026
Welcome to Cafe Diem, the Annapolis Coffee Crawl fueled by Visit Annapolis & Anne Arundel County. Your next coffee obsession starts here. Spend the week sipping your way through Annapolis with everything from handcrafted lattes and cold brews to espresso martinis and creative coffee inspired treats at some of the area’s favorite cafes and restaurants. Whether you are fueling up for the morning or winding down by the waterfront, there is always something brewing nearby.
The best part? Every stop earns you 100 points toward exciting prizes, and with prizes at 600 points, all you need is six delicious stops to claim your reward. You can only check in at each location once per day, but that just means you have the perfect excuse to grab a morning coffee and try somewhere new for an espresso martini at night.
Once you have earned enough points, prizes can be claimed at the Visit Annapolis & Anne Arundel County Visitor Center between 10:00 AM and 5:00 PM. So grab your friends, map out your must visit spots, and get ready to turn your coffee run into an Annapolis adventure!
Included Venues
See locations on an interactive map.
49 West Coffeehouse, Winebar & Gallery
49 West Coffeehouse, Winebar & Gallery invites you to savor handcrafted coffee, curated wines, and artful moments in the heart of Annapolis. Nestled on West Street, this welcoming spot blends a cozy cafe atmosphere with a refined winebar experience, offering artful exhibitions, live events, and a rotating menu of light bites. Whether you’re stopping by for a morning pick-me-up, an afternoon glass, or an evening with friends, 49 West pairs warm hospitality with a creative, community-driven vibe.
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Bean Rush Café
Bean Rush Café is a cozy, locally loved spot at 112 Annapolis St, Annapolis, MD 21401. Known for its aromatic coffees, handcrafted espresso drinks, and fresh baked pastries, this friendly café invites you to relax with a quick, energizing pick-me-up or settle in for a small, café-style bite. A convenient stop for locals and visitors alike, Bean Rush blends warm ambiance with flavorful, accessible menu options.
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Blackwall Hitch
Blackwall Hitch at 400 6th St in Annapolis offers a lively waterfront dining experience featuring a modern American menu, craft cocktails, and views of Spa Creek. Known for its welcoming atmosphere, it pairs coastal-inspired dishes with a vibrant bar scene, making it a popular spot for locals and visitors alike.
Bread and Butter Kitchen
Bread and Butter Kitchen is a cafe in Eastport, Maryland serving breakfast and lunch daily. In addition to our daily menu, we create delicious meals-to-go featuring local ingredients. Stop in for a quick bite with an amazing view!
True to our roots, we incorporate products from local farmers and makers into our menu.
Cafe Olé
Cafe Olé at 33 1/2 West St in Annapolis offers a warm, inviting atmosphere where locally sourced coffee, artisan pastries, and savory bites come together for a relaxed café experience. Whether you're popping in for a quick espresso, catching up with friends, or enjoying a quiet corner with a book, this cozy spot delivers friendly service and a welcoming vibe.
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Caliente Grill
Caliente Grill at 907 Bay Ridge Rd, Annapolis, MD 21403 offers a vibrant dining experience with bold, flavorful Mexican-inspired dishes, fresh ingredients, and warm hospitality. Enjoy tasty tacos, sizzling fajitas, and signature margaritas in a welcoming atmosphere that celebrates colorful, sunlit coastal charm. Perfect for casual meals with friends and family, featuring hearty staples, dietary options, and attentive service.
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Carpaccio Tuscan Kitchen & Wine Bar
Carpaccio Tuscan Kitchen & Wine Bar is a vibrant dining destination in the heart of Annapolis, offering a Tuscan-inspired menu of fresh, thoughtfully prepared dishes paired with an extensive selection of wines. Located at 1 Park Place, this stylish venue invites guests to savor handmade pastas, flavorful antipasti, and seasonal specials in a warm, inviting atmosphere perfect for intimate dinners, gatherings, and weekend escapes.
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Curate Annapolis Cafe & Bakery
Curate Annapolis Cafe & Bakery at 141 West St Ste 101 brings a polished, neighborhood bakery experience to Annapolis. Enjoy handmade pastries, fresh-brewed coffee, and seasonal dishes crafted with locally sourced ingredients in a warm, modern setting overlooking historic West Street. A welcoming spot for quick bites, relaxed gatherings, and anytime treats.
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Drummer's Lot Pub
Drummer's Lot Pub is a welcoming neighborhood tavern nestled on Church Circle in Annapolis, MD. Known for its cozy, wood-accented interior and casual atmosphere, the pub offers a curated menu of comforting American bites, a rotating lineup of local craft beers, and friendly service. A beloved stop for locals and visitors alike, Drummer's Lot provides a relaxed gathering spot just steps from historic waterfront streets, inviting guests to unwind with good food, great drinks, and comfortable camaraderie.
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Federal House Bar & Grille
Eatery in historic Annapolis offering New American Tavern & Seafood Fare with Dining Room, Cocktail/ Bar Area, Private banquet Room and Shaded / Heated year Round Open Patio.
Service Options: Weekday Happy Hour · Live Acoustic Music and Late Nite Dancing Fri & Sat · Sports on Televisions
Galway Bay Irish Restaurant and Pub
Galway Bay Irish Restaurant and Pub at 63 Maryland Ave in Annapolis blends authentic Irish hospitality with a warm, inviting atmosphere. Enjoy hearty favorites like shepherd’s pie, Irish stew, and fresh seafood, complemented by a carefully curated selection of Irish whiskeys and craft beers. With live music, friendly staff, and riverside views just steps from the historic downtown, it’s a welcoming spot for meal, drink, and camaraderie. Sláinte!
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Great Harvest Bread Company
An Annapolis ICON, celebrating 25 years in this location! Great Harvest Annapolis is all about scratch-made, wholesome, handmade, and never boring! From gourmet breads to our wide variety of mouthwatering goodies, there's always something for everyone and for every occasion-- all made with real ingredients and whole grain wheat from Montana's golden triangle.
InGrano Bistro Bakery
InGrano Bistro Bakery is a welcoming café and bakery located at 302 Harry S. Truman Pkwy Ste H in Annapolis, MD. Known for its warm, artisanal breads, flaky pastries, and handcrafted dishes, the bistro blends Italian-inspired flavors with fresh, locally sourced ingredients. Ideal for a quick breakfast, a cozy coffee break, or a casual meal, InGrano offers a inviting atmosphere, friendly service, and a menu that highlights made-from-scratch goodness.
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Leeward Market
Leeward Market at 601 Second St in Annapolis, MD offers a curated assortment of fresh essentials, local staples, and everyday conveniences set in a welcoming neighborhood hub. Enjoy easy, friendly service and convenient access in the heart of Annapolis.
Leo Annapolis
Leo is a locally owned, New American restaurant and bar located in the vibrant Arts District of downtown Annapolis. It features local flavors from nearby farms and purveyors to create a modern, seasonal and sustainable menu. We also have a full bar spotlighting local distilleries, breweries and wine. It is a comfortable and casual space where everyone is welcome to gather, with a mission of supporting other local, small businesses.
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Level a Small Plates Lounge
Level a Small Plates Lounge at 69 West St in Annapolis offers a stylish, intimate vibe with inventive small plates, craft cocktails, and a curated selection of wines. Enjoy seasonally inspired dishes, artful presentation, and attentive service in a modern, welcoming space that’s perfect for intimate dinners, post-work mingling, or a night out with friends.
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Luna Blu Ristorante Italiano
Luna Blu Ristorante Italiano invites you to savor authentic Italian flavors in the heart of Annapolis. Nestled at 36 West Street, this charming eatery blends classic regional dishes with a modern coastal charm, offering handmade pastas, wood-fired delights, and a curated selection of wines. Experience warm hospitality, a stylish ambiance, and a menu that celebrates the timeless pleasures of Italian dining. Buon appetito.
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Marmo Annapolis
Marmo Annapolis at 80 Compromise Street offers a refined selection of marble and stone surfaces for kitchens, baths, and living spaces, blending timeless craftsmanship with modern design in the heart of Annapolis.
Miss Shirley's Cafe, Annapolis
Miss Shirley's Café in Annapolis invites you to savor vibrant Southern-inspired comfort food in a convivial, retro-chic setting. Nestled at 1 Park Place, the restaurant serves hearty brunch, flavorful staples, and creative cocktails, delivering warm hospitality and a lively atmosphere that honors Southern tradition with a modern twist.
Oscar's Coffee
Oscar's Coffee, located at 105 Eastern Ave in Annapolis, MD, offers warm, welcoming vibes with a focus on craft coffee and locally sourced pastries. Whether you’re grabbing a quick espresso before a stroll along the harbor or settling in for a relaxed afternoon, this neighborhood spot blends friendly service with cozy atmosphere and thoughtful seasonal flavors.
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Parley Room
Parley Room at 25 State Circle in Annapolis offers an intimate, historic-inspired setting perfect for private gatherings, small conferences, and refined events. Featuring classic décor, flexible seating, and modern amenities, it combines old-world charm with contemporary convenience, making it an elegant backdrop for memorable occasions in Maryland’s capital.
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Preserve
Preserve is a casual American restaurant in Downtown Annapolis with a seasonal and sustainable focus. Pickling, preserving, and fermenting is also a passion and focus on the menu.
Rams Head Tavern
Rams Head Tavern, tucked along Annapolis’ historic West Street at 33 West Street, MD, is a classic Maryland venue renowned for its lively gastropub fare, live music, and warm, nautical-inspired ambiance. People flock for chef-driven pub dishes, signature crab dip, craft beers, and top-tier performances by local and touring artists in an intimate setting that captures the spirit of Annapolis.
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Red Red Wine Bar + Bistro
Red Red Wine Bar + Bistro invites you to unwind with a curated selection of wines, craft cocktails, and seasonal small plates in a warm, welcoming setting on Annapolis’s historic Main Street. Savor attentive service, live music nights, and stylish, convivial vibes perfect for date nights, friends, or a relaxed weeknight escape. Located at 189 B Main St, Annapolis, MD 21401.
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Rise Up City Dock
Rise Up City Dock at 25 Market Space sits along Annapolis’ historic waterfront, offering a welcoming gateway to maritime charm and city views. This vibrant hub blends convenient access to dining, shopping, and culture with a thriving community vibe, making it a perfect starting point for harbor strolls, sunset reflections, and memorable waterfront experiences.
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Seasalt Annapolis
Seasalt Annapolis offers a charming coastal-inspired collection in the heart of downtown Annapolis, blending nautical fashions, breezy accessories, and thoughtful gifts. Located at 1 Park Place, Suite 7, the shop embodies a relaxed, welcoming vibe with curated pieces perfect for seaside weekends and stylish everyday wear.
Sweet Hearts Patisserie
Sweet Hearts Patisserie is a cozy, inviting bakery nestled in Annapolis, MD, offering handmade pastries, delicate tarts, and luscious desserts crafted with seasonal ingredients. Located at 1410 Forest Dr, this charming shop welcomes guests with friendly service, elegant decorations, and a tempting selection that’s perfect for treating yourself or sharing with friends.
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The Admirals Cup Annapolis
The Admirals Cup Annapolis, located at 142 Dock St in the heart of Annapolis, MD, blends classic waterside charm with modern hospitality. Diners enjoy fresh, locally inspired seafood and seasonal coastal fare in a welcoming, nautical-inspired setting just steps from the Chesapeake Bay. Whether you’re stopping in for a breezy lunch, a leisurely dinner, or an intimate celebration, the restaurant captures the spirit of Annapolis with warm service, craft cocktails, and a memorable harbor-side experience.
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The Choptank
The Choptank, nestled along Annapolis’s historic waterfront at 110 Compromise Street, blends classic maritime charm with modern comfort. This inviting venue offers fresh, locally inspired dishes, craft cocktails, and warm hospitality in a nautical setting, perfect for casual bites, sunset views, and memorable gatherings on Maryland’s famed chesapeake coast.
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