What comes to mind when you think of October-fall foliage, football, and Halloween, right? Well, it’s all here. In the beautiful Annapolis countryside, family-friendly festivals abound. Think hayrides, big fat pumpkins, corn mazes, and all the things that make this time of year memorable for kids. For grown-up kids or youngsters who can handle a spine-tingling thrill, check out Annapolis' haunted tours. You'll be spooked by centuries-old tales of Annapolis' long-deceased inhabitants. When it comes to fun fall traditions, you can't beat Navy Football. Join the crowd at the Navy-Marine Corps Memorial Stadium and embrace the tradition and excitement that permeates the stands. If you're a sailor, boater, or just dreaming of getting on the water, come to our fall Boat Shows. On consecutive weekends, the U.S. Powerboat Show (October 3 thru 6) and the 50th anniversary of the U.S. Sailboat Show (October 10 thru 14) present two of the most extravagant, in-water boat shows in the nation.

Maryland Renaissance Festival
When: Weekends through October 20th; 10:00 a.m. – 7:00 p.m.
Where:1821 Crownsville Road, Annapolis

The region’s premier outdoor event and second largest Renaissance Festival in the country is celebrating its 40th season at Revel Grove. Travel back in time as you immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court. The festival includes 200+ entertainers, ten stages, a 3,000 seat jousting arena, 122 craft shops, 48 food and beverage emporiums, games, attractions and 85 acres of complimentary parking. Let merriment abound! Visit www.rennfest.com for more information.

Renaissance Festival

First Sunday Arts Festival
When: Sunday, October 6th, 2019 (and every first Sunday through November) 11:00 a.m. to 5:00 p.m.
Where: First block of West and Calvert Streets, Annapolis
Admission: Free

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West Street and Calvert Street next to Whitmore parking garage. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets. Visit our events page for more information.

Greenstreet Gardens Fall Festival
When: Saturday and Sunday, September 21st, 2019 - October 27th, 2019
Where: Greenstreet Gardens, 391 West Bay Front Road, Lothian, MD 20711

Six weekends of fall festivities is back and even better than before! Come enjoy different themed events and activities each weekend with family and friends. The 5-acre corn maze, pumpkin bowling, jumping pillow, haunted hay ride, cow train, giant teepee, corn box, straw castle, underground slide and more is everything you could ever imagine!

 Girl on Tractor

U.S. Powerboat Show
When: Thursday-Sunday, October 3rd-6th, 2019
Where: City Dock, Annapolis
Admission: Adult, $18-48; Child, $5; 6 and under, free

The nation’s oldest and largest in-water powerboat exhibition features everything from luxurious motor yachts and trawlers to high-performance boats and offshore fishing machines. The show includes family cruisers, center consoles, inflatables and the world's largest power catamaran section. Attendees will also find a wide selection of marine equipment, high-tech electronics, accessories, gear, and related services. Visit our events page for more information.

U.S. Sailboat Show
When: Thursday-Monday, October 10th-14th, 2019
Where: City Dock, Annapolis
Admission: Adult, $18-$35; Child, $5; 6 and under, free

Now in its 50th year, the nation’s oldest and largest in-water sailboat show featuring exclusively new boats attracts more than 50,000 boating enthusiasts from around the world to America’s Sailing Capital each year. The event is recognized worldwide as the premier sailing showcase for seminars, boating attire and accessories, foul weather gear and boats of all sizes. Visit our events page for more information.

Powerboat Show

Annual Pumpkin Walk
When: October 25th, 2019
Where: Hammond-Harwood House, 19 Maryland Avenue, Annapolis, MD
Admission: $15 per family/$10 per member family

An Annapolis tradition, children celebrate the Halloween season with games and crafts, a friendly story-telling witch, candy, and a costume parade around the 18th century mansion. Beer and wine is for sale for the grown-ups. A sppoky and fun time awaits your family, so register today! Click here to learn more.

Oyster Festival
When: Sunday, October 20th, 2019; 12:30 p.m. to 5:00 p.m.
Where: Captain Avery Museum, 1418 East West Shady Side Road, Shady Side
Admission: Adults, $6; children under 12, $2

Enjoy food, live music by local artists, unique crafts, face painting, and demonstrations showing the vital role oysters play in maintaining the health of the Chesapeake Bay. Seafood lovers are invited to feast on raw and fried oysters, oyster stew, fried oyster roll sushi, cream of crab soup, Maryland crab soup, and much more. Hamburgers and hotdogs will also be available. The day also includes the Avery Café and bake sale. Visit our events page for more information.

 Discover additional lodging options located just 30 minutes from Annapolis and 10 minutes to Baltimore, check out TheHotelsAtBWI.com.

Additional October Links

  • US Sailboat Show

    US Sailboat Show

    The United States Sailboat Show takes over the Annapolis Harbor October 10th through the 14th.

    Learn more
  • US Powerboat Show

    US Powerboat Show

    Debuting in 1970, the Annapolis Boat Shows have wowed boating enthusiasts for over forty years.

    Learn more
  • Renaissance Festival

    Renaissance Festival

    One of Maryland's most anticipated events of the summer, the Renaissance Festival has a little something for everyone in the family.

    Learn more