Festivals in Annapolis

Check out happening festivals events all around Annapolis, MD

35th Annual Kunta Kinte Heritage Festival

Sat, 13 Sep at 10:00 am Navy–Marine Corps Memorial Stadium

Lily Grace Live @ Annapolis Songwriters Festival 2025

 Fri, 12 Sep at 07:00 pm 33 West St, Annapolis, MD 21401-2574, United States

BAYGRASS 2025: Annapolis Baygrass Music Festival 9/20-21

 Sat, 20 Sep at 10:00 am 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

Tango Reo Quintet at Annapolis City Dock Tango

 Sat, 06 Sep at 08:00 pm Annapolis City Dock

Annapolis Fall Italian Festa

 Sun, 21 Sep at 10:00 am 620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401

SAT 9/20/25: BATMAN DAY 2025 AT THIRD EYE

 Sat, 20 Sep at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Four80East

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

Boatyard Beach Bash

 Sat, 20 Sep at 04:00 pm 723 2nd St, Annapolis, MD, United States, Maryland 21403

Herman's Hermits Starring Peter Noone (7:30PM)

 Sun, 28 Sep at 07:30 pm Rams Head On Stage

Dustbowl Revival w/ Chris Kasper

 Sun, 07 Sep at 08:00 pm Rams Head On Stage

Al Jardine and The Pet Sounds Band

 Sat, 13 Sep at 08:00 pm Maryland Hall

West Annapolis Oktoberfest 2025

 Sun, 28 Sep at 11:00 am Annapolis Street, Annapolis, MD, United States, Maryland 21401

Jimmie's Chicken Shack @ Maryland Seafood Festival

 Sat, 13 Sep at 03:00 pm Maryland Seafood Festival

10,000 Maniacs

 Sat, 13 Sep at 08:30 pm Rams Head On Stage

Annapolis Pride Parade and Festival

 Sat, 18 Oct at 10:00 am Maryland Hall

Stand Up Comedy Night at The Lounge @ Stan and Joe's Saloon

 Fri, 19 Sep at 07:00 pm Stan & Joe's Saloon USD 23

Eastport Yacht Club Lights Parade

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

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

Full Moon Celebration - October

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

First Sunday Arts Festival

Sun, 07 Sep at 11:00 am Calvert and West Streets, Annapolis, MD, United States, Maryland 21401

b.en & callum toner @ red red wine bar for annapolis songwriters festival

 Thu, 11 Sep at 09:00 pm Red Red Wine Bar

The Amish Outlaws

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

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

Annapolis Songwriters Festival with Watermark Songwriter On The Severn

 Sat, 13 Sep at 07:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

TBHB @ Dinner Under the Stars

 Sat, 13 Sep at 06:00 pm Main Street Annapolis

Full Moon Celebration - December

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

TBHB @Graduate Annapolis

Fri, 12 Sep at 08:00 pm Graduate Annapolis

Annapolis Pride Parade!

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

Annapolis Maryland Pride

 Sat, 18 Oct at 10:00 am Maryland Hall

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

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

Skerryvore

 Sun, 07 Sep at 07:00 pm Rams Head On Stage

Pickleball for Paws

 Fri, 12 Sep at 12:30 pm Truxton Park Rd, Annapolis, MD 21403, United States

2025 Drug Education and Awareness Sporting Festival

 Sat, 13 Sep at 11:00 am Annapolis Recreation & Parks

Annapolis Baygrass Festival TAP TAKEOVER at Stan & Joe's

 Sat, 13 Sep at 01:00 pm Stan and Joe's Saloon

PARKING: Military Bowl

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

Annapolis Songwriters Festival - Platinum Pass

 Thu, 11 Sep at 05:00 pm Rams Head On Stage

Annapolis Sailboat Show

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

The Crabtown Frolic

 Sat, 27 Sep at 11:00 am 19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

Full Moon Celebration - November

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

The Carole King & James Taylor Story

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

SAMHAIN- 2025

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

The Peake Run- Sandy Point Beach Run

 Sun, 14 Sep at 10:30 am Sandy Point Rd, Annapolis, MD 21409, United States

Annapolis Chocolate Binge Festival

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

The Doug Segree Band at 49 West

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

Skipjack Race Watch Party on MILDRED BELLE

 Sun, 14 Sep at 11:00 am Sandy Point State Park USD 13 to 45

Annapolis First Sunday Arts Festival w/ The Accidental Poet

 Sun, 07 Sep at 11:00 am West St, Annapolis, MD 21401, United States

Our Best-Ever Annapolis Sailboat Show!

 Thu, 09 Oct at 11:00 am Ego Alley

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

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

Pete Correale at Rams Head On Stage

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

TBHB @Ram’s Head Patio

Fri, 12 Sep at 01:00 pm Rams Head Tavern - Annapolis

Cruise to OysterFest in St. Michaels

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

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

Fall Fling With Bling

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

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

The Hot Sardines

 Wed, 17 Sep at 07:00 pm Rams Head On Stage

Kitchen Dwellers in Annapolis

 Sat, 20 Sep at 02:00 pm Sandy Point State Park

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

 Mon, 20 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

Burning Witches

 Tue, 16 Sep at 07:00 pm Rams Head On Stage

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