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Oct. 04, 2025 8:30 a.m. - 11:30 a.m.

St. Michaels Farmers Market

Downtown St. Michaels

Food & Drink, Health & Wellness, Kids & Family

The St. Michaels Farmers Market (SMFM) is a non-profit, producer-only farmers market in charming St. Michaels on Maryland’s Eastern Shore, located downtown at 206 South Talbot Street, and taking place on Saturdays from April through November betw... Read more

St. Michaels Farmers Market

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Oct. 04, 2025 9:00 a.m. - 1:00 p.m.

A.Y.C.E. BRUNCH @ Cult

Cult Classic Brewing Company

Food & Drink

Feast your wallet on the hottest deal in town. CULT CLASSIC introduces an All-You-Can-Eat Brunch from 9am - 1pm every Saturday & Sunday. Load your plate with with all the eggs, bacon, sausage and UNCH you can handle. We've also got some waffle... Read more

Unch

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Oct. 04, 2025 1:00 p.m. - 3:00 p.m.

Wilma Lee Heritage Cruises

Annapolis Maritime Museum

Lectures and Talks

Experience Annapolis and the Chesapeake Bay like never before on this guided two-hour heritage tour aboard the historic Skipjack Wilma Lee. Learn about the city’s history and the ecology of the Bay while viewing landmarks like the Chesapeake Bay ... Read more

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Oct. 04, 2025 1:00 p.m. - 3:00 p.m.

Wilma Lee Sunset Cruises

Annapolis Maritime Museum

Food & Drink, Lectures and Talks

Join our crew for a two-hour extraordinary cruise enjoying the golden hour on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned cocktails and soda). Note: this cruise also takes place every Friday night as well as Thursday... Read more

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Oct. 05, 2025 6:00 a.m. - 6:00 p.m.

Lifeline 100 Bicycle Event

Kinder Farm Park

Charities & Fundraisers, Health & Wellness, Kids & Family

Join Anne Arundel County Department of Recreation & Parks, Anne Arundel County Police, and Bicycle Advocates for Annapolis and Anne Arundel County (BikeAAA) for the 11th annual Lifeline 100 Community Bicycle Event! This award-winning event wel... Read more

Anne Arundel County Department of Recreation and Parks

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Oct. 05, 2025

Maryland Renaissance Festival

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Oct. 05, 2025 9:00 a.m.

GiGi's Playhouse Pickleball Tournament

The Dink / The Put Away

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Oct. 05, 2025 9:00 a.m. - 10:00 a.m.

Yoga on the Farm

Maryland Therapeutic Riding

Health & Wellness, Kids & Family

Embrace tranquility surrounded by our beautiful horses and serene farm landscape. Yoga is for everyone and can be done while seated or standing. All abilities are welcome! Farm tours are available following yoga for all interested. 2025 Dates ... Read more

Yoga Class Instagram Post (Real Estate Flyer) - 1

MTR

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Oct. 09, 2025 - Oct. 13, 2025

Annapolis Sailboat Show

Annapolis City Dock

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Oct. 09, 2025 2:00 p.m. - 4:00 p.m.

Flowerpot Snack n' Paint Xperience

Easton Visitor's Center

Art & Galleries

Jennifer Hartfield

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Oct. 11, 2025

Maryland Renaissance Festival

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Oct. 11, 2025 8:30 a.m. - 11:30 a.m.

St. Michaels Farmers Market

Downtown St. Michaels

Food & Drink, Health & Wellness, Kids & Family

St. Michaels Farmers Market

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Oct. 11, 2025 9:00 a.m. - 1:00 p.m.

A.Y.C.E. BRUNCH @ Cult

Cult Classic Brewing Company

Food & Drink

Unch

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Oct. 11, 2025 1:00 p.m. - 3:00 p.m.

Wilma Lee Heritage Cruises

Annapolis Maritime Museum

Lectures and Talks

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Oct. 11, 2025 7:00 p.m. - 11:00 p.m.

Crystal Ship (The Doors Tribute) LIVE at Cult

Cult Classic Brewing Company

Concerts & Live Music, Food & Drink

Step back in time to the vibrant Sunset Strip in the swinging 1960s with Crystal Ship, the ultimate and definitive tribute to The Doors. Immerse yourself in the music, magic, and intensity of a live Doors concert as this highly acclaimed act take... Read more

Doors

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Oct. 12, 2025

Maryland Renaissance Festival

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Oct. 14, 2025 6:00 p.m. - 7:30 p.m.

Books & Beers 2025

Cult Classic Brewing Company

Food & Drink, Lectures and Talks

Books and Beers returns with another Blockbuster lineup of new and Cult Classic reads for 2025.  This event is free and open to all who have read (You do not have to be 21). We discuss the book and questions about it for the first hour and sp... Read more

CLub

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Oct. 16, 2025 2:00 p.m. - 4:00 p.m.

Flowerpot Snack n' Paint Xperience

Easton Visitor's Center

Art & Galleries

Jennifer Hartfield

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Oct. 18, 2025

Maryland Renaissance Festival

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Oct. 18, 2025 - Oct. 19, 2025

US National Oyster Festival

St. Mary's County Fairgrounds

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