Annapolis Festivals Events

35th Annual Kunta Kinte Heritage Festival

Navy–Marine Corps Memorial Stadium 13 Sep 2025

Dinner Under the Stars - Let's Salsa Latin Fest

West Street and Calvert Street (Intersection), Annapolis, MD, United States, Maryland 21401 16 Aug 2025

Hello Kitty Cafe Truck East - Annapolis Appearance

Annapolis Mall 16 Aug 2025

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

1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409 20 Sep 2025

Summer Sidewalk Sale 2025

2512 A Solomons Island Road Annapolis, Maryland 21401 16 Aug 2025

Dustbowl Revival w/ Chris Kasper

Rams Head On Stage 7 Sep 2025

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

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 23 Aug 2025

Skerryvore

Rams Head On Stage 7 Sep 2025

Back to School Event at Festival at Riva

2323 Forest Dr, Annapolis, MD, United States, Maryland 21401 23 Aug 2025

Full Moon Celebration - October

Unitarian Universalist Church of Annapolis 3 Oct 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 26 Oct 2025

Naptown Flea

24 Market Space 24 Aug 2025

2nd Annapolis Wine and Dine

Susan Campbell Park 16 Aug 2025

The Blue Genies at Rams Head On Stage

Rams Head On Stage 30 Aug 2025

Tango Reo Quintet at Annapolis City Dock Tango

Annapolis City Dock 6 Sep 2025

Annapolis Fall Italian Festa

620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401 21 Sep 2025

Carpool: The Ultimate CARS Tribute Band

Rams Head On Stage 24 Aug 2025

Full Moon Celebration - September

Unitarian Universalist Church of Annapolis 5 Sep 2025

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

Rams Head On Stage 28 Sep 2025

Pops in the Park - Quiet Waters Park

Quiet Waters Park Rd, Annapolis, MD 21403, United States 31 Aug 2025

Eastport Yacht Club Lights Parade

Historic Downtown Annapolis 13 Dec 2025

Wine Down at the Farm

Historic Goshen Farm & Educational Center 17 Aug 2025

2025 Drug Education and Awareness Sporting Festival

Annapolis Recreation & Parks 13 Sep 2025

Pete Correale at Rams Head On Stage

Rams Head On Stage 7 Nov 2025

Jimmie's Chicken Shack @ Maryland Seafood Festival

Maryland Seafood Festival 13 Sep 2025

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

Stan & Joe's Saloon 19 Sep 2025

Four80East

Rams Head On Stage 24 Oct 2025

The Machine Performs Pink Floyd Unplugged

Rams Head On Stage 20 Aug 2025

Full Moon Celebration - December

Unitarian Universalist Church of Annapolis 5 Dec 2025

Songwriters In The Round- Friday

Rams Head On Stage 12 Sep 2025

Annapolis Pride Parade and Festival

Maryland Hall 18 Oct 2025

Lori McKenna

Rams Head On Stage 4 Oct 2025

T4D at 49 West

49 West Coffeehouse, Winebar & Gallery 31 Aug 2025

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

Annapolis Maritime Museum & Park 20 Aug 2025

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 7 Sep 2025

Lily Grace Live @ Annapolis Songwriters Festival 2025

33 West St, Annapolis, MD 21401-2574, United States 12 Sep 2025

Baltimore-Washington Shenandoah Harmony All-Day Singing

Annapolis Friends Meeting, Quakers 4 Oct 2025

Fun Day!

89 Bennion Road, 21402 16 Aug 2025

Songwriters In The Round- Saturday

Rams Head On Stage 13 Sep 2025

Annapolis Powerboat Show

Annapolis City Dock 2 Oct 2025

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

Rams Head On Stage 6 Oct 2025

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 7 Dec 2025

Annapolis Sailboat Show

Annapolis City Dock 9 Oct 2025

Full Moon Celebration - November

Unitarian Universalist Church of Annapolis 7 Nov 2025

Skipjack Race Watch Party on MILDRED BELLE

Sandy Point State Park 14 Sep 2025

Annapolis Songwriters Festival - Platinum Pass

Rams Head On Stage 11 Sep 2025

SAMHAIN- 2025

Unitarian Universalist Church of Annapolis 1 Nov 2025

The Peake Run- Sandy Point Beach Run

Sandy Point Rd, Annapolis, MD 21409, United States 14 Sep 2025

Unity Rhythm and Drum Circle

Unity by the Bay (Maryland) 25 Aug 2025

Barktoberfest Annapolis 2025

1906 Towne Centre Blvd 4 Oct 2025

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

Great Frogs Winery 9 Oct 2025

Kids on the Creek

Truxton Park Boat Ramp 24 Aug 2025

Annapolis Maryland Pride

Maryland Hall 18 Oct 2025

Annapolis First Sunday Arts Festival w/ The Accidental Poet

West St, Annapolis, MD 21401, United States 7 Sep 2025

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025

The Jerry Douglas Band

Rams Head On Stage 5 Nov 2025

PARKING: Military Bowl

Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025

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

Bloomsbury Sq, Annapolis, MD 21401, United States 28 Aug 2025

Annapolis First Sunday Arts Festival w/ The Accidental Poet

West St, Annapolis, MD 21401, United States 5 Oct 2025

The Amish Outlaws

Rams Head On Stage 16 Oct 2025

Fall Fling With Bling

2747 Riva Rd 22 Oct 2025

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

Rams Head On Stage 23 Nov 2025

Parking Military Bowl

Navy-Marine Corps Memorial Stadium 27 Dec 2025

Our Best-Ever Annapolis Sailboat Show!

Ego Alley 9 Oct 2025

THE PANCAKE PEEPS @ Annapolis Vintage Market

40 Hudson st unit 107 Annapolis Md 5 Oct 2025

The Hot Sardines

Rams Head On Stage 17 Sep 2025

2025 Annapolis Chamber Music Festival

St. Martin's Evangelical Lutheran Church 16 Aug 2025

Kitchen Dwellers in Annapolis

Sandy Point State Park 20 Sep 2025

Annapolis Powerboat Show

Annapolis City Dock 1 Oct 2025

Burning Witches

Rams Head On Stage 16 Sep 2025

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

Sandy Point State Park 23 Nov 2025