Annapolis Songwriters Festival

22 Sizzling Summer Family Concert

Chesapeake Children’s Museum, Annapolis, Saturday, July 22

August

Begins Saturday, September 14

Curated by Rams Head Presents and BMI, the annual multi-day music festival celebrates the art of songwriting. For an actionpacked weekend each September, songwriting artists and performers descend on Annapolis bars, restaurants, hotels, music venues, and stages to delight live music lovers with their latest creations. Modeled after the hugely successful Key West Songwriters Festival, the inaugural 2022 Annapolis Songwriters Festival saw Jake Owen, Amos Lee, Lucinda Williams, Fantastic Negrito, and countless other acts play at free and paid venues throughout Maryland’s capital city.

3 USNA Anchors Aweigh Music Tour

U.S. Naval Academy, Annapolis, Thursdays, August 3 and 10

4 Rotary Club of Annapolis Crab Feast

Navy-Marine Corps Memorial Stadium, Annapolis, Friday, August 4

12 USNA Student Youth Leadership Program

U.S. Naval Academy, Annapolis, Saturday, August 12

13 Carriages on West Street–Annapolis Corvette Show West Street, Downtown Annapolis, Sunday, August 13

17 Annapolis Art Walk Downtown Annapolis, Thursday, August 17

26 Maryland Renaissance Festival Crownsville, Saturdays, Sundays, and Labor Day, August 26October 22

27 Annapolis Ten-Mile Run Starts at Navy-Marine Corps Memorial Stadium, Annapolis, Sunday, August 27

September

14 Annapolis Songwriters Festival Downtown Annapolis, ThursdaySunday, September 14-17

23 Kunta Kinte Heritage Festival Annapolis, Late September (date to be announced)

23 Maryland Seafood Festival

Sandy Point State Park, Annapolis, Saturday-Sunday, September 23-24 (tentative)

24 West Annapolis Oktoberfest West Annapolis, Sunday, September 24

24 Bay Bridge Paddle Begins at Sandy Point State Park, Annapolis, Sunday, September 24 (tentative)

30 Annapolis Baygrass Music Festival

Sandy Point State Park, Annapolis, Saturday-Sunday, September 30-October 1

October

Arts in the Park Chesapeake Arts Center, Brooklyn Park, A Saturday in October TBD

1 Great Annapolis Pumpkins Downtown Annapolis, Month of October

1 Lifeline 100 Bicycle Event Starts at Kinder Farm Park, Millersville, Sunday, October 1

Insider’s tip–Live! Casino & Hotel Maryland is home to The Hall at Live!—a stunning 75,000-squarefoot entertainment venue that hosts sporting events, concerts, headline acts, and more.

13 USNA Anchors Aweigh

Music Tour

U.S. Naval Academy, Annapolis, Thursdays, July 13 and 27

14 Farm to Table Series with Graze Gourmet Wildberry Farm & Market, Crownsville, Second and Fourth Fridays, July 14October 27

7 September Sunsets Concert Series Annapolis Maritime Museum and Park, Annapolis, Thursdays, September 7-28

9 Boatyard Beach Bash Annapolis Maritime Museum and Park, Annapolis, Saturday, September 9

9 U.S. Naval Academy football vs. Wagner Seahawks

Navy-Marine Corps Memorial Stadium, Annapolis, Saturday, September 9

13 Anne Arundel County Fair Anne Arundel County Fairgrounds, Crownsville, Wednesday-Sunday, September 13-17

5 Special Historic Hauntings Walking Tour Departs 25 Market Space in Downtown Annapolis, Thursdays-Saturdays in October

5 United States Powerboat Show Annapolis City Dock, Thursday-Sunday, October 5-8

12 United States Sailboat Show Annapolis City Dock, Thursday-Sunday, October 12-15

14 Captain Avery Oyster Festival Captain Avery Museum, Shady Side, Saturday, October 14

14 Harvest Hootenanny Chesapeake Children’s Museum, Annapolis, Saturday, October 14

20 Scarecrow Stroll

Inner West Street, Downtown Annapolis, Friday, October 20-Wednesday, November 1

JOE TOOLAN, Chair,

21 U.S. Naval Academy football vs. Air Force Falcons Navy-Marine Corps Memorial Stadium, Annapolis, Saturday, October 21

21 Fall Fest on West Inner West Street, Downtown Annapolis, Saturday, October 21

22 Maryland Avenue Fall Festival Maryland Avenue and State Circle, Downtown Annapolis, Sunday, October 22

27 Pumpkin Walk Hammond-Harwood House, Annapolis, Friday, October 27

28 Day of the Dead/Dia de los Muertos Festival Maryland Hall for the Creative Arts, Annapolis, Saturday, October 28

November

Annapolis Jazz & Roots Festival Eastport, November (tentative)

Bay Bridge Run/Walk Annapolis to Stevensville, A Sunday in November (tentative)

4 Maritime Republic of Eastport Tug of War Spa Creek, Saturday, November 4 (tentative)

5 Maryland STEM Festival

Chesapeake Children’s Museum, Annapolis, Sunday, November 5

16 Lights & Leashes Dog Walk

Sandy Point State Park, Annapolis, Thursday-Friday, November 16-17

Pride Board of Directors

18 Dashing through the Snow 5K Fun Run

Sandy Point State Park, Annapolis, Saturday, November 18

19 Lights On the Bay Drive through Light Show

Sandy Point State Park, Annapolis, Sunday, November 19-Monday, January 1

25 Small Business Saturday Downtown Annapolis, Saturday, November 25

26 Grand Illumination Market Space, Downtown Annapolis, Sunday, November 26

December

Military Bowl Navy-Marine Corps Memorial Stadium, Annapolis, (tentative)

1 Jolly Express Cruise Annapolis City Dock, Weekends in December

1 Holiday Candlelight Stroll Departs 25 Market Space, Downtown Annapolis, Fridays and Saturdays in December

2 State House by Candlelight Maryland State House, Annapolis, Saturday, December 2 (tentative)

2 Historic Annapolis Colonial Yuletide Celebration

William Paca House and Garden and Hogshead, Annapolis, Saturday, December 2

3 Chocolate Binge Festival West Street, Downtown Annapolis, Sunday, December 3

7 Annapolis Holiday Market Downtown Annapolis, Thursday-Sunday, December 7-10

7 Midnight Madness Holiday Shopping Downtown Annapolis, Thursdays, December 7, 14, 21

8 Live Arts Maryland–Celebration of Christmas Maryland Hall for the Creative Arts, Annapolis, Friday, December 8

9 Eastport Yacht Club Lights Parade Annapolis City Dock/ Spa Creek, Saturday, December 9

9 Kwanzaa Celebration Banneker-Douglass Museum, Annapolis, Saturday, December 9

9 Vintage Christmas Market Wildberry Farm & Market, Crownsville, Saturdays, December 9 and 16

15 Live Arts Maryland–Handel’s Messiah St. Anne’s Church, Annapolis, Friday-Sunday, December 15-17

16 Santa Speedo Run Saturday, December 16, (tentative)

31 Annapolis New Year’s Eve Celebration Downtown Annapolis, Sunday, December 31