Sultana Education Foundation's Downrigging Weekend Tall Ship and Bluegrass Festival
October 27th through 29th; Main Street, Chestertown
Sultana’s Downrigging Weekend and Bluegrass Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast and is combined with 3 days of live bluegrass music and entertainment. Visitors to the festival can expect to see a waterfront packed with ships, schooners, and wooden boats; performances by world-class musicians; lectures by nationally recognized authors and filmmakers; plenty of opportunities to go sailing as part of a fleet of “Tall Ships”; and the chance to spend the weekend in Chestertown – one of America’s best preserved historic seaports.
October 27th, 4-6 p.m.; Hammond Harwood House, Annapolis
This event will also feature a brief tour of the mansion to introduce children to colonial superstitions and the special architecture of the Hammond-Harwood House. Wear your best costume for the selfie station! This family event is an Annapolis tradition not to be missed! Costumes encouraged. Beer and wine will be available for purchase.
SOFO Free Drive In Movie Night
October 27th, 7 p.m.; Bay Ridge Shopping Center
The free SOFO drive in movie nights are back starting July 28th with Free Movies shown on the side of the Bay Ridge Shopping Center wall next to the Eastport library Live music with Nate Finn starts at 7 pm with movie shown after at dusk. This month's movie is Corpse Bride.
October 28th; Chesapeake Bay Maritime Museum, St Michaels
Get ready to sip, slurp, and savor at the Chesapeake Bay’s favorite fall festival! The event features live music on two stages, boat rides, retriever demonstrations, oysters and other local fare, an oyster stew competition and cooking demonstrations, along with children’s activities, oyster demonstrations, harvesting displays and Chesapeake-related documentary screenings.
26th Annual Academy Art Museum Annual Craft Show
October 28th through 29th; Academy Art Museum, Easton
The Academy Art Museum’s 26th Annual Craft Show will feature over 60 artists from across the United States on October 28 & 29, 2023, with a special Preview Event on October 27. All proceeds from fees and generous community sponsorships directly support the Museum’s mission of providing meaningful art experiences and education to the Mid-Shore. The Academy Art Museum Craft Show team looks forward to welcoming artists from all craft categories and will work with artists to insure the broadest possible reach with our patrons.
October 28th; Downtown Centreville
Centreville Day is a free family fall festival featuring interactive activities for the whole family. All event features are free of charge. The event draws 1,200 to 1,500 attendees from Queen Anne’s County and surrounding Eastern Shore counties, and is great for businesses and non-profits who wish to do outreach to families.
October 28th, 10 a.m. to 2 p.m.; Columbia Gateway, Columbia
Attend Howard County’s first Veteran Owned Small Biz Expo to celebrate Howard County Business Appreciation Week and National Veteran’s Small Business Appreciation Week. Sponsored by the Howard County Office of Veterans and Military Families, come experience veteran owned small businesses, live entertainment, vendors, food, and activities.
October 28th, 11 a.m. to 4 p.m.; West Belle Street, Ridgely
Mac and Cheese Festival! We are celebrating five years of a ghouda thing! 10 chefs compete for your vote to the best mac and cheese! They will earn a title and a cool $1000 in cash. We have VIP tickets, food, beer, games and lots of great vendors!
Annearrundell County Free School 300th Family Fun Festival
October 28th, 1 to 4 p.m.; Annearrundell County Free School Museum, Davidsonville
Go back to school, back in time, at Maryland's oldest one-room schoolhouse. Meet 18th-century school teachers and enjoy docent tours, storytelling, American colonial-era crafts & games and authentic refreshments - free family fun to commemorate the Free School's 300th Anniversary (1723-2023).
October 28th, 5:30 p.m.; Chesapeake Bay Environmental Center, Grasonville
Spend your Saturday listening to live music, eating from all the different food stations and taking part in the Auctions. You are invited to the “2nd Annual Rock the Reef event at the Chesapeake Bay Environmental Center. Saturday October 28th from 5:30 – 8:30 join in for this under the tent event on CBEC’s Grounds.
The Brick Companies Zombie Dash
October 29th, 10 a.m.; Smithsonian Environmental Research Center, Edgewater
Join us at The Brick Companies' Zombie Dash 5k, complete with a Kids Fun Run and an Inflatable Costume Mad Dash! Expect a scenic route dotted with zombies, finish-line medals, exclusive participant shirts, a lively "Skele-bration" Zone with treats and vendors, and a complimentary drink for 5k runners — it's a festive gathering suitable for everyone.
Anne Arundel Community College Open House
November 1st, 5 p.m.; Anne Arundel Community College, Arnold
We’re rolling out the red carpet and invite you to start your adventure at our open house. Tour our campus, meet with faculty and students, talk with admissions and financial aid representatives. Experience hands-on demonstrations, visit classrooms and labs, and learn more about our degrees, certificates and skilled trades programs.
