Annapolis Food & Drink Events

Annapolis First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 3 May 2026

Southern (Harwood)Class of 1986 40th Reunion

Annapolis, Maryland 26 Sep 2026

Great Frogs Wine Tasting to Benefit the Navy SEAL Foundation

Great Frogs Winery 27 Sep 2026

Comedy Fundraiser

914 Bay Ridge Ave, Annapolis, MD 26 Sep 2026

Party in the Port 2026

317 First St, Annapolis, MD, United States, Maryland 21403 17 Oct 2026

Chart House Prime - Rodney Strong Wine Dinner

Chart House Prime 15 Oct 2026

LIVE MUSIC with Michael McHenry Tribe

Blackwall Hitch - Annapolis 2 Oct 2026

The Taste: Celebrate the Chesapeake in Maryland

The Atreeum at Soaring Timbers 24 Sep 2026

🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷

7 Church Cir, Annapolis, MD, United States, Maryland 21401 23 Sep 2026

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

Carpaccio Tuscan Kitchen & Wine Bar 18 Aug 2026

Annapolis Chocolate Binge Festival

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

St. John’s Block Party

970 St. John’s Drive, Annapolis, MD 21409 24 Oct 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Bountiful Harvest - Costumes & Cocktails

10 Hudson St, Annapolis, MD, United States, Maryland 21401 23 Oct 2026

Chart House Prime - Caymus Wine Dinner

Chart House Prime 5 Nov 2026

Navy Midshipmen Tailgate Party

Captain's Daughter 10 Oct 2026

New Date: Heavy Seas Beer Dinner

400 6th St, Annapolis, MD, United States, Maryland 21403 22 Sep 2026

Italian Week at Sweet Hearts Patisserie!

1410 Forest Dr, Annapolis, MD, United States, Maryland 21403 6 Oct 2026

Founders' Friendsgiving

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

Feast on the Farm: A Celebration of Conservation

Mas Que Farm 24 Oct 2026

Annapolis Outback Presents: Canvas, Cocktails and Cuisine!

Outback Steakhouse 15 Oct 2026

Fall Saturdays at Ridge Grow

244 Old Mill Bottom Rd S , Annapolis, MD, United States, Maryland 21409 10 Oct 2026

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

Great Frogs Winery 21 Oct 2026

Here's to Heroes!

155 Main St, Annapolis, MD, United States, Maryland 21401 6 Oct 2026

🏡🍦 Madison Apartments Welcomes ELLO Gelato Bar for a Sweet Monday Evening! 🍦🌿

1000 Madison St, Annapolis, MD 21403-2200, United States 21 Sep 2026

Foodies + New Friends: Annapolis Dinner + Coffee Club

Restaurant of the Week 1 Apr 2026

LIVE MUSIC with Bravenoise

Blackwall Hitch - Annapolis 18 Dec 2026