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Happening Next in Annapolis

Upcoming Festivals Events

Maryland Renaissance Festival at Maryland Renaissance Festival

 Maryland Renaissance Festival 27 Sep 2026
FESTIVALS

Annapolis Sailboat Show - October 2026

 Annapolis City Dock 15 Oct 2026
CALENDAR

36th Annual Kunta Kinte Heritage Festival

 Navy–Marine Corps Memorial Stadium 26 Sep 2026
FESTIVALS

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Upcoming Food & Drinks Events

Annapolis First Sunday Arts Festival

Calvert and West Streets, Annapolis, MD, United States, Maryland 21401 3 May 2026
FESTIVALS

Southern (Harwood)Class of 1986 40th Reunion

Annapolis, Maryland 26 Sep 2026
WORKSHOPS

Great Frogs Wine Tasting to Benefit the Navy SEAL Foundation

 Great Frogs Winery 27 Sep 2026
FOOD-DRINKS USD 60

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Upcoming Live Music Events

Michael Franti Trio

 Rams Head On Stage 28 Sep 2026

Margo Price at Rams Head On Stage

 Rams Head On Stage 2 Oct 2026

Los Lonely Boys

 Rams Head On Stage 28 Sep 2026
CALENDAR

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Upcoming Comedy Events

Josh Blue at Rams Head On Stage

 Rams Head On Stage 15 Oct 2026

Sean Hayes at Rams Head On Stage

 Rams Head On Stage 23 Sep 2026
TRIPS-ADVENTURES

Comedy Fundraiser

 914 Bay Ridge Ave, Annapolis, MD 26 Sep 2026
COMEDY

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Upcoming Trunk Or Treat Events

Fall Fest

 Alder Rd, Annapolis, MD 21402, United States 23 Oct 2026
FESTIVALS

Fall Saturdays at Ridge Grow

244 Old Mill Bottom Rd S , Annapolis, MD, United States, Maryland 21409 10 Oct 2026
FOOD-DRINKS

Tri-Ward Trunk or Treat

 The Church of Jesus Christ of Latter-day Saints 27 Oct 2026
FITNESS FREE

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Upcoming Parades Events

Annapolis Pride

Annapolis, MD 3 Oct 2026
PARADES

Party in the Port 2026

 317 First St, Annapolis, MD, United States, Maryland 21403 17 Oct 2026
MUSIC

Candice Carnival Creations for Annapolis Pride

 Downtown Annapolis Partnership 3 Oct 2026
FITNESS USD 55

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Trending Events in Annapolis

AACSPCA's Trick or Treat Trail

 SPCA of Anne Arundel County 24 Oct 2026
FITNESS USD 5

Halloween Spooktacular!

 St. John's College 25 Oct 2026
FITNESS USD 0 TO 28

The Annapolis Powerboat Show

Annapolis Boat Show 8 Oct 2026

North Texas Mean Green at Navy Midshipmen Football at Navy Marine Corps Memorial Stadium

 Navy Marine Corps Memorial Stadium 2 Sep 2026
SPORTS

Annapolis Sailboat Show

 Annapolis City Dock 7 Oct 2026
TRIPS-ADVENTURES

Tulsa Golden Hurricane at Navy Midshipmen Football at Navy Marine Corps Memorial Stadium

 Navy Marine Corps Memorial Stadium 10 Oct 2026
SPORTS

Los Lonely Boys at Rams Head On Stage

 Rams Head On Stage 29 Sep 2026
TRIPS-ADVENTURES

MarineMax Kent Island at The Annapolis Boat Show

 Annapolis City Dock 8 Oct 2026
FITNESS FREE

Author Event: Jeneva Rose

 Maryland Hall 25 Sep 2026
ART

Anthony Rodia at Rams Head On Stage

 Rams Head On Stage 3 Oct 2026

Tulsa Golden Hurricane at Navy Midshipmen Football Tickets

 Navy-Marine Corps Memorial Stadium 10 Oct 2026
SPORTS EUR 51

Centerpieces & S'mores - SOLD OUT

244 Old Mill Bottom Rd S , Annapolis, MD, United States, Maryland 21409 23 Sep 2026
WORKSHOPS

Five for Fighting with String Quartet at Rams Head On Stage

 Rams Head On Stage 18 Oct 2026
TRIPS-ADVENTURES

Navy Midshipmen vs. Tulsa Golden Hurricane

 Navy Marine Corps Memorial Stadium 9 Oct 2026
TRIPS-ADVENTURES

Southern Culture On the Skids at Rams Head On Stage

 Rams Head On Stage 26 Sep 2026
CALENDAR
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