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

Dinner Under the Stars - Let's Salsa Latin Fest

Sat, 16 Aug at 04:00 pm West Street and Calvert Street (Intersection), Annapolis, MD, United States, Maryland 21401

Hello Kitty Cafe Truck East - Annapolis Appearance

 Sat, 16 Aug at 10:00 am Annapolis Mall

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

Summer Sidewalk Sale 2025

 Sat, 16 Aug at 10:00 am 2512 A Solomons Island Road Annapolis, Maryland 21401

Dustbowl Revival w/ Chris Kasper

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

SAT 8/23/25: THIRD EYE KIDS COMIC DAY

 Sat, 23 Aug at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Skerryvore

 Sun, 07 Sep 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

2nd Annapolis Wine and Dine

 Sat, 16 Aug at 01:00 pm Susan Campbell Park USD 29 to 45

Naptown Flea

 Sun, 24 Aug at 01:00 pm 24 Market Space Free

The Blue Genies at Rams Head On Stage

 Sat, 30 Aug at 08:00 pm Rams Head On Stage

Tango Reo Quintet at Annapolis City Dock Tango

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

2025 Drug Education and Awareness Sporting Festival

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

Annapolis Fall Italian Festa

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

Carpool: The Ultimate CARS Tribute Band

 Sun, 24 Aug at 08:00 pm Rams Head On Stage

Full Moon Celebration - September

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

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

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

Pops in the Park - Quiet Waters Park

 Sun, 31 Aug at 05:30 pm Quiet Waters Park Rd, Annapolis, MD 21403, United States

Eastport Yacht Club Lights Parade

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

Wine Down at the Farm

 Sun, 17 Aug at 04:00 pm Historic Goshen Farm & Educational Center

Four80East

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

Pete Correale at Rams Head On Stage

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

The Machine Performs Pink Floyd Unplugged

 Wed, 20 Aug at 08:00 pm Rams Head On Stage

Annapolis Pride Parade and Festival

 Sat, 18 Oct at 10:00 am Maryland Hall

Jimmie's Chicken Shack @ Maryland Seafood Festival

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

Lori McKenna

 Sat, 04 Oct at 08:00 pm Rams Head On Stage

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

Full Moon Celebration - December

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

Songwriters In The Round- Friday

 Fri, 12 Sep at 07:00 pm Rams Head On Stage

Back to School Event at Festival at Riva

 Sat, 23 Aug at 01:00 pm 2323 Forest Dr, Annapolis, MD, United States, Maryland 21401

First Sunday Arts Festival

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

T4D at 49 West

 Sun, 31 Aug at 07:00 pm 49 West Coffeehouse, Winebar & Gallery

Exclusive Movie Screening -- Death On The Chesapeake: A Hard Rain

 Wed, 20 Aug at 05:00 pm Annapolis Maritime Museum & Park USD 15

Lily Grace Live @ Annapolis Songwriters Festival 2025

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

Baltimore-Washington Shenandoah Harmony All-Day Singing

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

Fun Day!

 Sat, 16 Aug at 11:00 am 89 Bennion Road, 21402

Songwriters In The Round- Saturday

 Sat, 13 Sep at 11:00 am Rams Head On Stage

Annapolis Sailboat Show

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

Annapolis Powerboat Show

 Thu, 02 Oct at 10:00 am Annapolis City Dock

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

 Mon, 06 Oct at 07:00 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

Full Moon Celebration - November

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

Skipjack Race Watch Party on MILDRED BELLE

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

Annapolis Songwriters Festival - Platinum Pass

 Thu, 11 Sep at 05:00 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

Unity Rhythm and Drum Circle

 Mon, 25 Aug at 06:30 pm Unity by the Bay (Maryland)

Barktoberfest Annapolis 2025

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

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

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

Our Best-Ever Annapolis Sailboat Show!

 Thu, 09 Oct at 11:00 am Ego Alley

Kids on the Creek

 Sun, 24 Aug at 11:00 am Truxton Park Boat Ramp

Annapolis Maryland Pride

 Sat, 18 Oct at 10:00 am Maryland Hall

Annapolis First Sunday Arts Festival w/ The Accidental Poet

 Sun, 07 Sep 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

The Jerry Douglas Band

 Wed, 05 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

Bloomsbury Square | No Harm Annual Community Service Resource Pop-Up

 Thu, 28 Aug at 03:00 pm Bloomsbury Sq, 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

Fall Fling With Bling

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

The Amish Outlaws

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

Live Dead and Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers

 Sun, 23 Nov at 08:00 pm Rams Head On Stage

Parking Military Bowl

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

THE PANCAKE PEEPS @ Annapolis Vintage Market

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

The Hot Sardines

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

2025 Annapolis Chamber Music Festival

 Sat, 16 Aug at 07:30 pm St. Martin's Evangelical Lutheran Church

Kitchen Dwellers in Annapolis

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

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