Week of October 29–November 4
Live Arts Maryland Golf Classic • Bay Hills Golf Club (Oct. 29)
A golf fundraiser supporting Live Arts Maryland. Check-in at 8 a.m.; play begins at 9 a.m.
Halloween Whodunit 3 • Rams Head on Stage (Oct. 29)
A murder-mystery comedy with a Halloween theme.
Very Superstitious! Paca House tours (Oct. 29–31)
Explore colonial superstitions on a guided house tour.
Café Scientifique (Oct. 29) • 49 West
A science talk about Chesapeake osprey and the challenges they face.
Naptown Flea Halloween Night Market • Annapolis (Oct. 30)
The Curious Savage • Severn (Oct. 30–31)
A stage comedy about an unexpected inheritance and the meaning of kindness.
Disney’s Frozen the Broadway Musical • Children’s Theatre of Annapolis (Oct. 30–Nov. 1)
Annapolis Opera Presents The Pirates of Penzance • Maryland Hall (Oct. 30 & Nov. 1)
Pumpkin Walk • Hammond-Harwood House (Oct. 30) • Family-friendly
Halloween games, crafts, storytelling and a costume parade.
Lonesome October Vol. 2 • 49 West (Oct. 30)
Live music with Teller Vision, The Prince II, and Scott of the Andes with Brandon Walker. Doors at 7:30 p.m.; show at 8 p.m.
Día de los Muertos at Maryland Hall (Oct. 31) • Family-friendly
Celebrate with music, dance, altars, art and food.
Tavern Talk (Oct. 31) • Hogshead Trades Museum
Explore the history of Annapolis’s Revolutionary-era taverns.
Greenstreet Fall Fest (Oct. 31 & Nov. 1) • Lothian • Family-friendly
Corn maze, hayrides and farm activities, 10:30 a.m.–5 p.m.; last admission at 4 p.m.
More music at 49 West
Badger Band (Oct. 31)
Gary Wright & Leah Weiss (Nov. 1)
Backroom Sessions: Skribe & Early Worm (Nov. 2)
Unified Jazz Ensemble (Nov. 3)
Dave Chappell & Friends (Nov. 4)
Free Motown Concert • Annapolis (Oct. 31) • Family-friendly
The Gunston School Open House • Centreville (Nov. 1)
First Sunday Arts Festival • Annapolis (Nov. 1)
Honoring Maryland’s Emancipation Day • Museum of Historic Annapolis (Nov. 1) • Family-friendly
Guided history tours, crafts and a Book Nook mark Maryland’s Emancipation Day.
Minecraft Creator: Team Design Challenge • Gambrills (Nov. 2) • Ages 7–14
A one-day Minecraft design camp for ages 7–14.
Navy Men’s Soccer vs American • Glenn Warner Soccer Facility (Nov. 3)
Gaelic Storm • Rams Head on Stage (Nov. 4)
A live Celtic music performance.





Eye on Annapolis: Top 5 in the News | Oct. 27, 2026 |