Annapolis Food & Drink Events

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 6 Dec 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Pretty Big Deal Plays Tastings & Tunes

West St, Annapolis, MD 21401, United States 14 Nov 2026

Brunch With The Grinch

California Pizza Kitchen at Annapolis 12 Dec 2026

Noche de Karaoke Night: Duet Edition at Caliente Grill

Caliente Grill 6 Nov 2026

National Pupusa Day — Weekend Celebration!

Caliente Grill 6 Nov 2026

Foodies + New Friends: Annapolis Dinner Club | Giving Back Edition

Carpaccio Tuscan Kitchen & Wine Bar 18 Aug 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Founders' Friendsgiving

Cooper's Hawk Winery & Restaurant- Annapolis 7 Nov 2026

Friendsgiving Salsa & Bachata Night at Caliente Grill

Caliente Grill 13 Nov 2026

Bead Bar at the Bar!- Jewelry Making Event at Dark Horse

Dark Horse 19 Nov 2026

LIVE MUSIC with MXD

Blackwall Hitch - Annapolis 21 Nov 2026

LIVE MUSIC with Timmie Metz Band

Blackwall Hitch - Annapolis 13 Nov 2026

FDOC End of Year Dinner.

Middleton Tavern 28 Nov 2026

Maryland Yuletide Weekend 2027

210 Holiday Ct 8 Jan 2027

Food Glorious Food: Class, Culture and Cooking in Colonial Annapolis

4 Pinkney St, Annapolis, MD 21401-1718, United States 14 Nov 2026

Foodies + New Friends: Annapolis Dinner + Coffee Club

Restaurant of the Week 28 Oct 2026

Women's Recipe Swap: Recipes, Stories & New Friends (Annapolis)

4th St, Annapolis, MD 21403, United States 16 Jan 2027

Hearts & Hatters Revelry Ball

126 West St, Annapolis, MD 21401-2880, United States 13 Feb 2027

LIVE MUSIC with Bravenoise

Blackwall Hitch - Annapolis 16 Oct 2026

Here's to Heroes!

155 Main St, Annapolis, MD, United States, Maryland 21401 3 Nov 2026

Happy Hour

2 Market Space, Annapolis, MD, United States, Maryland 21401 28 Oct 2026