Festivals in Annapolis

Check out happening festivals events all around Annapolis, MD

Barktoberfest Annapolis 2025

 Sat, 04 Oct at 11:30 am 1906 Towne Centre Blvd USD 0 to 13

Baltimore-Washington Shenandoah Harmony All-Day Singing

 Sat, 04 Oct at 10:00 am Annapolis Friends Meeting, Quakers Free

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

 Mon, 06 Oct at 07:00 pm Rams Head On Stage

Four80East

 Fri, 24 Oct at 07:00 pm Rams Head On Stage

Full Moon Celebration - November

 Fri, 07 Nov at 07:30 pm Unitarian Universalist Church of Annapolis

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

 Thu, 09 Oct at 06:00 pm Great Frogs Winery USD 29 to 45

The Amish Outlaws

 Thu, 16 Oct at 07:00 pm Rams Head On Stage

Full Moon Celebration - October

 Fri, 03 Oct at 07:30 pm Unitarian Universalist Church of Annapolis

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 26 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Annapolis Pride Parade and Festival

 Sat, 18 Oct at 10:00 am Maryland Hall

Annapolis Sailboat Show

 Thu, 09 Oct at 10:00 am Annapolis City Dock

Annapolis Maryland Pride

 Sat, 18 Oct at 10:00 am Maryland Hall

Eastport Yacht Club Lights Parade

 Sat, 13 Dec at 06:00 pm Historic Downtown Annapolis

Full Moon Celebration - December

 Fri, 05 Dec at 07:30 pm Unitarian Universalist Church of Annapolis

First Sunday Arts Festival

Sun, 05 Oct at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

Cruise to OysterFest in St. Michaels

 Sat, 25 Oct at 09:00 am 1 Dock St, Annapolis, MD, United States, Maryland 21401

The Carole King & James Taylor Story

 Sat, 15 Nov at 08:00 pm Rams Head On Stage

PARKING: Military Bowl

 Fri, 26 Dec at 07:00 pm Navy Marine Corps Memorial Stadium Parking Lots

SAMHAIN- 2025

 Sat, 01 Nov at 07:00 pm Unitarian Universalist Church of Annapolis

The Doug Segree Band at 49 West

Mon, 17 Nov at 07:30 pm 49 West St, Annapolis, MD 21401-2420, United States

Pete Correale at Rams Head On Stage

 Fri, 07 Nov at 08:00 pm Rams Head On Stage

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

Here's to Heroes!

Tue, 07 Oct at 10:00 am 155 Main St, Annapolis, MD, United States, Maryland 21401

U2topia: The Mid-Atlantic U2 Tribute Band

Fri, 28 Nov at 08:00 pm Rams Head On Stage

Dragonfest 2025

 Sat, 11 Oct at 12:00 pm Pier 4 Marina

Annapolis Pride Parade!

 Sat, 18 Oct at 09:30 am St Johns St, Annapolis, MD 21401, United States

Annapolis First Sunday Arts Festival w/ The Accidental Poet

 Sun, 05 Oct at 11:00 am West St, Annapolis, MD 21401, United States

The Empty Pockets at Rams Head On Stage

 Wed, 03 Dec at 08:00 pm Rams Head On Stage

Renaissance Festival - Annapolis

 Sat, 27 Sep at 02:00 pm Maryland Renaissance Festival

Fall Fling With Bling

 Wed, 22 Oct at 11:00 am 2747 Riva Rd Free

Taste of Fall on West Street

 Sun, 09 Nov at 02:00 pm 53 West St USD 7 to 82

THE PANCAKE PEEPS @ Annapolis Vintage Market

 Sun, 05 Oct at 11:00 am 40 Hudson st unit 107 Annapolis Md

Parking Military Bowl

 Sat, 27 Dec at 04:00 pm Navy-Marine Corps Memorial Stadium

Nutcracker Storytime at the William Paca Garden Featuring the Ballet Theatre of Maryland

 Sun, 12 Oct at 01:00 pm 186 Prince George St, Annapolis, MD 21401-1724, United States

Annapolis Powerboat Show

 Wed, 01 Oct at 07:00 pm Annapolis City Dock

Maryland Day Week 2026 - filled with fun events!

 Thu, 19 Mar at 10:00 am Anne Arundel County, MD, United States, Maryland

Wellness on the Green with Toastique Annapolis

 Thu, 17 Apr at 09:00 am Annapolis Town Center Free

2025 Lights on the Bay MD with the SPCA of Anne Arundel County

 Sun, 23 Nov at 05:00 pm Sandy Point State Park USD 23 to 100