Annapolis Festivals Events

Festivals Happening Next in Annapolis, MD

Full Moon Celebration - November

 Unitarian Universalist Church of Annapolis 7 Nov 2025
HEALTH-WELLNESS

Four80East

 Rams Head On Stage 24 Oct 2025
TRIPS-ADVENTURES

Annapolis Pride Parade and Festival

 Maryland Hall 18 Oct 2025
FESTIVALS

Eastport Yacht Club Lights Parade

 Historic Downtown Annapolis 13 Dec 2025
PARADES

Annapolis Sailboat Show

 Annapolis City Dock 9 Oct 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 2 Nov 2025
FESTIVALS

Annapolis Maryland Pride

 Maryland Hall 18 Oct 2025

✊March with PFLAG Southern Maryland at Annapolis Pride🏳️‍🌈

 College Ave, Annapolis, MD 21401, United States 18 Oct 2025
PARADES

Fall Fest

 1906 Towne Centre Boulevard, Annapolis, MD, United States, Maryland 21401 18 Oct 2025
FESTIVALS

Cruise to OysterFest in St. Michaels

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

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

SAMHAIN- 2025

 Unitarian Universalist Church of Annapolis 1 Nov 2025

Annapolis Jazz & Roots Festival - Michael McHenry Tribe

 Pip Moyer Recreation Center at Truxtun Park 9 Nov 2025
MUSIC

The Doug Segree Band at 49 West

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

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

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

Annapolis Chocolate Binge Festival

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

Trunk or Treat

 Eucalyptus Rd, Annapolis, MD 21402, United States 24 Oct 2025
TRUNK-OR-TREAT

Pete Correale at Rams Head On Stage

 Rams Head On Stage 7 Nov 2025

U2topia: The Mid-Atlantic U2 Tribute Band

Rams Head On Stage 28 Nov 2025
ENTERTAINMENT

Annapolis Pride Parade Watch Party

 138 West Street, Annapolis, MD, United States, Maryland 21401 18 Oct 2025
PARTIES

Dragonfest 2025

 Pier 4 Marina 11 Oct 2025

The Empty Pockets at Rams Head On Stage

 Rams Head On Stage 3 Dec 2025
CALENDAR

Annapolis Pride Parade!

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

Harvest Festival - FREE

 Roger W "Pip" Moyer Community Recreation Center at Truxtun Park, 273 Hilltop Ln, Annapolis, MD, United States, Maryland 21403 25 Oct 2025
FESTIVALS

Fall Fling With Bling

 2747 Riva Rd 22 Oct 2025
ART FREE

Annapolis Jazz & Roots Festival JC Jefferson - Salute to Quincy Jones

 Banneker-Douglass-Tubman Museum 8 Nov 2025
MUSIC

Taste of Fall on West Street

 53 West St 9 Nov 2025
MUSIC USD 7 TO 82

Pressing Strings

 Rams Head On Stage 28 Dec 2025
MUSIC

The Great Annapolis Gingerbread Houses Contest

 26 West St, Annapolis, MD 21401-2421, United States 22 Nov 2025
CONTESTS

Here's to Heroes!

155 Main St, Annapolis, MD, United States, Maryland 21401 7 Oct 2025
FESTIVALS

Renaissance Festival - Annapolis

 Maryland Renaissance Festival 11 Oct 2025
FESTIVALS

Jay Hurtt VI of Little Bird w/ Skribe

 Rams Head On Stage 17 Dec 2025
MUSIC

Parking Military Bowl

 Navy-Marine Corps Memorial Stadium 27 Dec 2025
CALENDAR

The Young Dubliners: The HOT TODDY Tour

 Rams Head On Stage 10 Feb 2026
MUSIC

Maryland Day Week 2026 - filled with fun events!

 Anne Arundel County, MD, United States, Maryland 19 Mar 2026

Burning Witches

 Rams Head On Stage 31 Mar 2026
TRIPS-ADVENTURES

Wellness on the Green with Toastique Annapolis

 Annapolis Town Center 17 Apr 2025
HEALTH-WELLNESS FREE

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