Annapolis Festivals Events

Festivals Happening Next in Annapolis, MD

35th Annual Kunta Kinte Heritage Festival

Navy–Marine Corps Memorial Stadium 13 Sep 2025
FESTIVALS

West Annapolis Oktoberfest 2025

 Annapolis Street, Annapolis, MD, United States, Maryland 21401 28 Sep 2025
OKTOBERFEST

Lily Grace Live @ Annapolis Songwriters Festival 2025

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

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

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

Annapolis Fall Italian Festa

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

Boatyard Beach Bash

 723 2nd St, Annapolis, MD, United States, Maryland 21403 20 Sep 2025
MUSIC

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

 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 20 Sep 2025
HOLIDAY

Four80East

 Rams Head On Stage 24 Oct 2025
TRIPS-ADVENTURES

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

 Rams Head On Stage 28 Sep 2025
ART

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

 Stan & Joe's Saloon 19 Sep 2025
COMEDY USD 23

Dustbowl Revival w/ Chris Kasper

 Rams Head On Stage 7 Sep 2025
ENTERTAINMENT

Jimmie's Chicken Shack @ Maryland Seafood Festival

 Maryland Seafood Festival 13 Sep 2025
FESTIVALS

Al Jardine and The Pet Sounds Band

 Maryland Hall 13 Sep 2025
MUSIC

10,000 Maniacs

 Rams Head On Stage 13 Sep 2025
FESTIVALS

Annapolis Pride Parade and Festival

 Maryland Hall 18 Oct 2025
FESTIVALS

Eastport Yacht Club Lights Parade

 Historic Downtown Annapolis 13 Dec 2025
PARADES

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

TBHB @ Dinner Under the Stars

 Main Street Annapolis 13 Sep 2025
FESTIVALS

Full Moon Celebration - October

 Unitarian Universalist Church of Annapolis 3 Oct 2025
HEALTH-WELLNESS

First Sunday Arts Festival

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

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

 Red Red Wine Bar 11 Sep 2025
FESTIVALS

The Amish Outlaws

 Rams Head On Stage 16 Oct 2025
TRIPS-ADVENTURES

Barktoberfest Annapolis 2025

 1906 Towne Centre Blvd 4 Oct 2025
DOG USD 0 TO 13

Baltimore-Washington Shenandoah Harmony All-Day Singing

 Annapolis Friends Meeting, Quakers 4 Oct 2025
POTLUCK FREE

Annapolis Songwriters Festival with Watermark Songwriter On The Severn

 1 Dock St, Annapolis, MD, United States, Maryland 21401 13 Sep 2025
FESTIVALS

Annapolis Maryland Pride

 Maryland Hall 18 Oct 2025

Full Moon Celebration - December

 Unitarian Universalist Church of Annapolis 5 Dec 2025
HEALTH-WELLNESS

TBHB @Graduate Annapolis

Graduate Annapolis 12 Sep 2025
FESTIVALS

Leftover Salmon (Acoustic Show) w/ Sicard Hollow

 Rams Head On Stage 6 Oct 2025
MUSIC

Skerryvore

 Rams Head On Stage 7 Sep 2025
TRIPS-ADVENTURES

Pickleball for Paws

 Truxton Park Rd, Annapolis, MD 21403, United States 12 Sep 2025
TOURNAMENTS

2025 Drug Education and Awareness Sporting Festival

 Annapolis Recreation & Parks 13 Sep 2025
FESTIVALS

Annapolis Baygrass Festival TAP TAKEOVER at Stan & Joe's

 Stan and Joe's Saloon 13 Sep 2025
FESTIVALS

PARKING: Military Bowl

 Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025
TRIPS-ADVENTURES

The Carole King & James Taylor Story

 Rams Head On Stage 15 Nov 2025
MUSIC

Annapolis Songwriters Festival - Platinum Pass

 Rams Head On Stage 11 Sep 2025
FESTIVALS

Annapolis Sailboat Show

 Annapolis City Dock 9 Oct 2025

The Crabtown Frolic

 19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 27 Sep 2025
ART

Full Moon Celebration - November

 Unitarian Universalist Church of Annapolis 7 Nov 2025
HEALTH-WELLNESS

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
FESTIVALS

Annapolis Chocolate Binge Festival

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

The Doug Segree Band at 49 West

49 West St, Annapolis, MD 21401-2420, United States 17 Nov 2025
ENTERTAINMENT

Skipjack Race Watch Party on MILDRED BELLE

 Sandy Point State Park 14 Sep 2025
SPORTS USD 13 TO 45

Annapolis First Sunday Arts Festival w/ The Accidental Poet

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

Our Best-Ever Annapolis Sailboat Show!

 Ego Alley 9 Oct 2025
CALENDAR

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

 Great Frogs Winery 9 Oct 2025
FOOD-DRINKS USD 29 TO 45

TBHB @Ram’s Head Patio

Rams Head Tavern - Annapolis 12 Sep 2025
FESTIVALS

Pete Correale at Rams Head On Stage

 Rams Head On Stage 7 Nov 2025

Annapolis Pride Parade!

 St Johns St, Annapolis, MD 21401, United States 18 Oct 2025
PARADES

Cruise to OysterFest in St. Michaels

 1 Dock St, Annapolis, MD, United States, Maryland 21401 25 Oct 2025
MUSIC

Annapolis First Sunday Arts Festival w/ The Accidental Poet

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

The Empty Pockets at Rams Head On Stage

 Rams Head On Stage 3 Dec 2025
CALENDAR

Fall Fling With Bling

 2747 Riva Rd 22 Oct 2025
ART FREE

THE PANCAKE PEEPS @ Annapolis Vintage Market

 40 Hudson st unit 107 Annapolis Md 5 Oct 2025

Parking Military Bowl

 Navy-Marine Corps Memorial Stadium 27 Dec 2025
CONTESTS

The Hot Sardines

 Rams Head On Stage 17 Sep 2025
TRIPS-ADVENTURES

Kitchen Dwellers in Annapolis

 Sandy Point State Park 20 Sep 2025
CONCERTS

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

 186 Prince George St, Annapolis, MD 21401-1724, United States 20 Oct 2025
ART

Annapolis Powerboat Show

 Annapolis City Dock 1 Oct 2025
MAGIC-SHOW

Burning Witches

 Rams Head On Stage 16 Sep 2025
TRIPS-ADVENTURES

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

 Sandy Point State Park 23 Nov 2025
HOLIDAY USD 23 TO 100