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October 17, 2026

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  2. You’re a Good Man, Charlie Brown – Presented by Compass Rose Theater

    Live Arts Studio Westfield Mall (mall entrance by the Container store), Annapolis, MD 21401, United States

    Charlie Brown – One Weekend ADDED After sold-out performances! Our Helen Hayes Recommended production of You’re A Good Man, Charlie Brown is extended through Oct. 18! Oct 15,16 & Oct…

    $15 – $55

  4. Inaugural Harvest Gala

    The Byzantium Event and Conference Center 2747 Riva Road, Annapolis, MD 21401, United States

    Join Lace ‘Em Up for Libby for an evening themed with flannel and jeans to support the fight against childhood cancer. Swamp Donkey NewGrass will be providing the music so…

8:00 am

  1. B.I.G. Book Sale

    B.I.G. Warehouse 451 Defense Highway, Annapolis

    Books for International Goodwill (BIG) invites you to join us for our book sales. Thanks to generous donations, we have many new titles to choose from in all categories. Discover…

    Free

10:00 am

  1. Elementary School Allowance Workshop

    CovingtonAlsina, 67 West St #200, Annapolis, MD 21401, USA West Street 67, Annapolis, Maryland 21401, United States

    Join us for a fun, hands-on workshop that teaches kids how to make and manage money. We’ll discuss the four things you can do with your money: Save, spend, give,…

    $25

  5. Oxon Hill Farm Fall Festival

    Oxon Hill Farm 6710 Oxon Hill Rd, Oxen Hill

    As the temperature drops and the leaves start to change, join us for the Oxon Hill Farm Fall Festival – live music, sheep dog demonstrations, pumpkin painting, and a Community Showcase…

    Free

  6. Art @ the Park 2026

    Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, Maryland 21403

    Enjoy live music, an outstanding display of art, including ceramics, woodworking, jewelry, and painting, along with demonstrations and a variety of food trucks. There will be art activities for young…

    $8

  7. U.S. National Oyster Festival

    St. Mary’s County Fairgrounds 42455 Fairgrounds Road, Leonardtown

    US National Oyster Shucking Championship, Tasting Tent, Stories from a Mermaid, educational exhibits, live performances.

    $50

  8. Annapolis Sailboat Show

    Annapolis City Dock Dock Street, Annapolis, Maryland 21401

    Walk the floating docks during the Annapolis Sailboat Show, climb aboard gleaming yachts and center consoles, and explore everything from family cruisers to weekend fishing rigs. Whether you’re boat-curious, shopping…

    $10 – $32

  9. Tilghman Island Day

    Tilghman Island 5979 Tilghman Island Rd, Tilghman

    Live music, Crab-picking, oyster-shucking, and boat-docking contests. Fresh seafood along with other food.

    Free

  10. Art @ the Park

    600 Quite Park Road, Annapolis, MD 21403 600 Quiet Waters Park Road, Annapolis, 21403, United States

    The Friends of Quiet Waters are hosting the 36th annual Art @ the Park fine arts festival on October 17th and 18th from 10:00am until 4:00pm each day. The Park…

    $8.00

11:00 am

  1. Featured: Doug Segree

    Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States

    Doug Segree brings more than 30 years of live performance experience to the Beer Farm, blending acoustic, rock, pop, and classic favorites into an engaging set built around strong vocals,…

  2. Rockville Antique and Classic Car Show

    Rockville Civic Center Park 603 Edmonston Drive, Rockville

    From Packard to Ferrari, the Rockville Antique and Classic Car Show showcases 33 car clubs, bringing together auto collectors and enthusiasts to share memories of classic cars from years past.…

    Free

  3. Berlin Oktoberfest

    Downtown Berlin Bay Street & Stephen Decatur Park, Berlin

    Authentic Oktoberfest music featuring the Lost Lederhosen Band and the Dunehounds. A variety of OKTOBERFEST food featuring brats and knockwurst, pretzels, German chocolate cake, pie, ice cream, smoothies & more!…

    Free

  4. American Indian Festival

    Patuxent River Park 16000 Croom Airport Road, Upper Marlboro

    The American Indian Festival is a vibrant celebration of Native American culture, heritage, and traditions, offering live music and traditional and contemporary dances of Native America. DIY arts and crafts…

    Free

  5. 18th Annual American Indian Festival

    Patuxent River Park 16000 Croom Airport Road, Upper Marlboro

    Celebrate Native American culture at the 18th Annual American Indian Festival, featuring traditional music, dance, crafts, food, storytelling, and family-friendly activities.

    Free

  6. Captain Avery Museum 2026 Oyster Fest

    Captain Avery Museum 1418 East West Shady Side Road, Shady Side, Maryland 20764

    Captain Avery Museum Oyster Festival October 17th 11:00 am- 5:30 pm Raindate: October 18th Tickets are now on sale for the Captain Avery Museum 2026 Oyster Festival! Join us on…

    $10 – $20

  7. Captain Avery Museum’s Oyster Festival

    Captain Avery Museum 1418 East West Shady Side Road, Shady Side, Maryland 20764

    Join Captain Avery Museum at their Oyster Festival! This event features good community company, fine regional music, an array of choice gifts for purchase, a cash raffle, local food and…

    $10 – $20

  8. Oktoberfest at Schifferstadt

    Schifferstadt Architectural Museum 1110 Rosemont Ave, Frederick

    Come enjoy great food and drink, lively German music, historic demonstrations, museum tours, and handmade products from many arts & crafts vendors. Our biggest event of the year!

    Free

12:00 pm

  1. Fall Fun Days

    Kinder Farm Park 1001 Kinder Farm Park Road, Millersville, Maryland

    Fall Fun and entertainment over two weekends. Scarecrow-making, hayrides, farm animals, family games, and trunk-or-treat.  Fee for some activities Saturday, October 17, 2026 From 12:00 PM to 3:00 PM Online…

    Free – $11.20

  2. DragonFest – October 17

    Pier 4 Marina 301 Fourth St, Annapolis, 21403, United States

    What do Dragon Boats, breast cancer survivors, and Spa Creek have in common? DragonFest 2026, the annual fundraiser for the Annapolis Dragon Boat Club! Come out to Pier 4 in…

    Free

  3. DC Wine Fest: Fall Edition!

    Union Market 1309 5th St NE, Washington, DC

    Introducing the DC Wine Fest®, a wine tasting experience that aims to stimulate all of your senses. Your ticket includes all wine tastings.

    $61.64

1:00 pm

  1. Middle School Financial Literacy Workshop

    CovingtonAlsina, 67 West St #200, Annapolis, MD 21401, USA West Street 67, Annapolis, Maryland 21401, United States

    This workshop is designed to help middle school students (ages 12-14) make educated financial decisions as they enter into the next phase of life. We’ll talk about how to manage…

    $25

  2. OktoBEARfest

    Maryland Zoo One Safari Place, Baltimore

    Kick off the weekend with a lively Friday night at OktoBEAR-Eve—an exclusive 21+ event featuring seasonal brews, festive vibes, and wild encounters (leave the cubs at home for this one).…

    $35 – $85

2:00 pm

  1. RocktoberFest

    Whalen Commons 19701 Fisher Avenue, Poolesville

    Annual Fall Festival featuring live music, local breweries, and plenty of kids activities!

    Free

4:00 pm

  1. Featured: Mike Heuer

    Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States

    Mark your calendars for this weekend at the Beer Farm, where Mike Heuer will take the stage with his unique blend of Alt/Folk-Pop! With 14 years of experience as a…

4:30 pm

  1. SpookyFest

    Bayhead Park 1661 Bay Head Rd, Annapolis

    SpookyFest brings back your absolute favorite traditions alongside brand-new, upgraded experiences the whole crew will love. Your favorite Fall Festival classics—like the Haunted House, Halloween movies in the theatre, and…

    $11 – $27

5:00 pm

  1. Haunted Hike and Trick or Treat Trail

    New Germany State Park 349 Headquarters Lane​​, Grantsville

    Celebrate the season by completing the Trick-or-Treat Trail for kids age 12 and under, or a Haunted Hike spooky adventure. Trick or Treat Trail for ages 12 and under. 5-6:30 p.m.…

    Free

6:30 pm

Ongoing

  1. Advantages of Services in AHD Clinic

    AHD Clinic 448 E 147th St, The Bronx, NY 10455, United States

    We are happy to announce a limited time event, 5-10% discount on any treatment, for all new patients. AHD Clinic 448 E 147th St The Bronx, NY 10455 (929) 999-1880

  2. Creative Circle – Monthly Meetup (2026)

    AND Creative Studio 1851 McGuckian St Suite B, Annapolis, United States

    Find your monthly creative adventure with like-minded creators in our monthly Creative Circle! Drop in or join us for all 5! * Aug. 13 * Sept. 10 * Oct. 1…

    $45 – $200

  4. La Sylphide

    Maryland Hall 801 Chase Street, Annapolis, Maryland 21401, United States

    A captivating tale of love and the supernatural with the Ballet Theatre of Maryland. Be transported to the rugged hills and misty skies of the Scottish Highlands in this quintessential…

    $36 – $62

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