Annapolis Fall Italian Festa 2026 Sun, 20 Sep at 10:00 am 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 NONPROFIT
Annapolis First Sunday Arts Festival Sun, 03 May Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 FESTIVALS
Great Frogs Wine Tasting to Benefit the Navy SEAL Foundation Sun, 27 Sep at 01:00 pm Great Frogs Winery USD 60 FOOD-DRINKS
Party in the Port 2026 Sat, 17 Oct at 06:00 pm 317 First St, Annapolis, MD, United States, Maryland 21403 MUSIC
Celebrate National Queso Day with Free Chips & Queso at California Tortilla Sun, 20 Sep at 11:00 am 2002 Annapolis Mall Rd Annapolis, MD 21401 FREE
Chart House Prime - Rodney Strong Wine Dinner Thu, 15 Oct at 07:00 pm Chart House Prime USD 120 FITNESS
The Taste: Celebrate the Chesapeake in Maryland Thu, 24 Sep at 06:00 pm The Atreeum at Soaring Timbers USD 50 TO 500 FITNESS
Foodies + New Friends: Annapolis Dinner Club | Giving Back Edition Tue, 18 Aug Carpaccio Tuscan Kitchen & Wine Bar USD 29 FITNESS
Annapolis Chocolate Binge Festival Sun, 06 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States FESTIVALS
Bountiful Harvest - Costumes & Cocktails Fri, 23 Oct at 07:00 pm 10 Hudson St, Annapolis, MD, United States, Maryland 21401 MUSIC
St. John’s Block Party Sat, 24 Oct at 12:00 pm 970 St. John’s Drive, Annapolis, MD 21409 ENTERTAINMENT
🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷 Wed, 23 Sep at 06:30 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401 MUSIC
New Date: Heavy Seas Beer Dinner Tue, 22 Sep at 06:00 pm 400 6th St, Annapolis, MD, United States, Maryland 21403 WORKSHOPS
Founders' Friendsgiving Sat, 07 Nov at 06:00 pm Cooper's Hawk Winery & Restaurant- Annapolis USD 71 THANKSGIVING
Feast on the Farm: A Celebration of Conservation Sat, 24 Oct at 03:00 pm Mas Que Farm USD 215 TO 269 FITNESS
Annapolis Outback Presents: Canvas, Cocktails and Cuisine! Thu, 15 Oct at 06:00 pm Outback Steakhouse USD 66 TO 349 FITNESS
Fall Saturdays at Ridge Grow Sat, 10 Oct at 01:00 pm 244 Old Mill Bottom Rd S , Annapolis, MD, United States, Maryland 21409 FOOD-DRINKS
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery Wed, 21 Oct at 06:00 pm Great Frogs Winery USD 23 TO 45 FOOD-DRINKS
Here's to Heroes! Tue, 06 Oct at 10:00 am 155 Main St, Annapolis, MD, United States, Maryland 21401 FESTIVALS
Foodies + New Friends: Annapolis Dinner + Coffee Club Wed, 01 Apr at 07:00 pm Restaurant of the Week USD 55 MEETUPS