Annapolis & Anne Arundel County welcomes you to explore over five hundred miles of beautiful shoreline and create their own unique Chesapeake Bay adventure. The crisp fall air awaits the Annapolis Boat Shows, excitement of a Navy Football Game, or a trip to the countryside to enjoy a pumpkin patch or local winery—the festivities are endless.  

Annapolis Powerboat/Sailboat Show
Image courtesy of Jarvin Hernandez.

 

Signature Events Lineup 

  1. Annapolis Powerboat Show (Downtown Annapolis) | October 3-6  

The City Docks of Annapolis will have waves of excitement as boat lovers from near and far return to celebrate the 50th anniversary of the U.S. Powerboat Show. Spend your days soaking up the eclectic atmosphere while shopping for everything from boat supplies to navigation gear and cool marine accessories. Don’t miss out on this unforgettable experience in America’s Sailing Capital! 🚤 

 

2. Arts in the Park (Brooklyn Park) | October 5 

Ready for artsy fun for everyone? The 10th Annual Arts in the Park festival is going to be bigger and better than ever! Imagine a day filled with creative art activities, local vendors, mouth-watering food trucks, live performances, and so much more—all for free! This event reigns in 1,000 community members and visitors together to celebrate, support, and connect through arts this fall! 🍂 

 

  1. Annapolis Sailboat Show (Downtown Annapolis) | October 10-14

Catch the tide at again four days after the U.S. Powerboat Show at the U.S. Sailboat Show for a celebration of all things sailing! Explore floating docks filled with sailboats from manufacturers around the world. Stroll along the dock to view multihulls, monohulls, cruisers, racers, and sailing dinghies for an Instagram-worthy post. You won’t want to miss out on show tents that line the shore, showcasing the latest nautical gear, electronics, communication tools, sails, rigging, and opportunities from charter companies and sailing clubs. 🌊 

 

  1. Great Annapolis Pumpkins (Annapolis) | October 5 – 31  

Have you ever seen 1,000-pound pumpkins around an 18th-century waterfront town? This unbelievable scene captures the heart of many on social media when using the hashtag #GreatAnnapolisPumpkins. The coolest part: just before Halloween these pumpkins will magically transform into carved jack-o-lanterns! This will be pumpkin to talk about, be sure to follow us on social media @VisitAnnapolis so you can view all the excitement of the Great Carving! 🎃 

 

  1. Fall Harvest Festival Featuring War of 1812 Remembrance (Pasadena) | October 13 

Dive into the rich history of African Americans during the War of 1812 and discover their pivotal contribution to Hancock’s Resolution. The day will fill with classic fall family fun with activities like scarecrow making, crafting corn husk dolls, and playing games. The festival will also have a live performance by The Chanteymen, a renowned group known for their lively old=time sea chanteys. It’s a perfect mix of education and fun! 🍂 

 

  1. Scarecrow Stroll (Annapolis) | October 19-November 2  

Picture eleven days of scarecrows lining the historic West Street of Annapolis—it's a sight you’ll never forget. Teams, schools, and businesses across Anne Arundel County create scarecrows dressed as Naval Midshipmen and even a mom out on a spa day. Cast your vote for the best-looking scarecrow starting on October 21st at Fall Fest on West! 

 

  1. Maryland Avenue Fall Festival (Downtown Annapolis) | October 20 

An Annapolis classic, meant for the entire family! The charming businesses of historic Maryland Avenue return for their annual Fall Fest featuring local-favs such as the Halloween Pup Parade, live music, exciting performances, and Halloween-themed activities for kids! Shop for local gems as you taste great food and wander through a beer garden, and so much more! 🐾 

 

  1. Visit an Anne Arundel County Farm or Fall Festival | October 1 –31  

Let’s face it, no fall season is complete without a visit to a local farm or festival! Spend a day picking pumpkins, shop for fall decor, and stopping by a Fall Festival at one of Anne Arundel County’s best farms, gardens, and nurseries. These local businesses, including Homestead Gardens, Greenstreet Gardens, Knightongale Farms, and Doepkens Farms, are at the heart of our community and offer unique fall experiences you will get FOMO from if missed! 🌾 

 

  1. Special Historic Hauntings Walking Tour (Annapolis) | Weekends (and some weekdays) 

Spooky season is here and ready to guide your spirit to a thrilling journey through the dark alleys, spooky side streets, and lesser-known haunted sites throughout Annapolis. After this spooky stroll, you might just have your own creepy story to add to Annapolis’s haunted history! 👻 

 

 

Man driving large blue tractor through sunflower field

 

Community Vibes & Festive Feels 

  1. Great Chesapeake Bay Schooner Watch Party (Annapolis) | October 3 

Join the Schooner Woodwind for an unforgettable watch party at the Great Schooner Race! Experience the thrill as 25 boats line up at the start for a 130-mile adventure from Annapolis to Norfolk! Grab your tickets for this one-of-a-kind experience in America’s Sailing Capital! 🌊 

 

  1. Macbeth (Annapolis) | October 3-13 

Experience one of Shakespeare's classic tragedies, Macbeth! This haunting play follows the ambitious Scottish general and his cunning wife as prophecy leads to murder and madness. Performances run Thursday to Sunday, with weekend matinees. 🎭 

 

  1. Lifeline 100 Bicycle Event (Millersville) | October 6 

Join cyclists of all ages and abilities at this annual event celebrating Anne Arundel County's scenic trails! The 10th anniversary of the century ride features a 15-mile route, raising funds for local nonprofits. Registration is now open! 🌟 

 

  1. USA BMX Chesapeake BMX East Coast Nationals (Severn) | October 11-13 

Don’t miss your chance to watch the excitement at the 2024 East Coast Nationals hosted by Chesapeake BMX! This is the Northeast's final opportunity to earn National points. Come cheer on your favorite racer or simply enjoy a thrilling weekend of fast-paced action. Curious about how they do it? Join us at the East Coast Nationals and see for yourself! 🚴‍♀️ 

 

  1. Captain Avery Oyster Festival (Shady Side) | October 12 

Join us for this annual waterfront festival, celebrating community, live regional music, delicious local food and drinks, and, of course, delectable oysters! With 26 years of history in Anne Arundel County, this award-winning festival offers a chance to snag donated goods and experiences at great prices. It’s a fall tradition everyone loves! 🥂 

 

  1. Arts at the Park (Quiet Waters) | October 12-13  

Check out one of Anne Arundel County’s stunning waterfront parks for a day of live music, demos, and amazing art! You’ll find everything from ceramics and jewelry to woodworking and photography up for grabs. It’s a perfect outing for the whole family—and don’t forget to bring your furry friend along! 🎨 

 

  1. Adaptive Family Sailing (Eastport) | October 17, 20 

If you’re looking for an unforgettable day on the Chesapeake Bay—look no further. Join Chesapeake Region Accessible Boating (C.R.A.B.) for a day of sailing! Sailing is a truly inclusive sport, allowing people of all abilities to share the experience together. Teaming up on the boat fosters rewarding moments that strengthen family bonds. Reach out to C.R.A.B. to book your free sailing adventure—spots are available on a first-come, first-served basis! ⛵ 

 

  1. U.S. Naval Academy Football vs. Chartlotte 49ers (Annapolis) | October 19 

Get ready for a show-down between Navy and UNC Charlotte right in Annapolis’ backyard at Navy-Marine Corps Memorial Stadium! The Midshipmen are hitting the field against the 49ers at 3:30 p.m. for this heated rivalry. Traveling from out of town? Plan your Navy football adventure today. 🏈 

 

  1. Tavern Talk and Tea: The Story of the Burning of the Peggy Stewart in Annapolis (Crownsville) | October 19 

Celebrate the 250th anniversary of the burning of the Peggy Stewart with the Rising Sun Inn! On October 19, 1774, rebels set fire to the ship and its cargo of tea right in Annapolis Harbor. Visit us for a brief talk sharing this fascinating piece of local history, followed by a delightful three-course tea. Don’t miss out on this unique historical experience! ☕ 

 

  1. 250th Anniversary of the Burning of the Peggy Stewart (Annapolis) | October 19 

Along the shores of Annapolis Harbor, experience a stunning drone show illuminating a tall ship that resembles a colonial-era merchant brig at the City Dock, where the Severn River meets the bay. Watch as the night sky lights up with a reenactment celebrating the anniversary of Annapolis’ historic ‘Tea Party.’ The show kicks off at 7 p.m.! 🚢 

 

  1. J/22 World Championship Regatta (Annapolis) | October 22-26 

Annapolis is a premier destination for regatta support, rivaled by only a few global sailing hubs. Its central location on the East Coast makes it the perfect spot for international sailing events. Come experience world-class sailing right from the shores of Maryland’s charming capital! Don’t forget to check out lodging options in downtown Annapolis.  

 

  1. Jug Bay Wetland Sanctuary's Halloween Critter Crawl (Lothian) | October 25 

A Halloween Critter Crawl? Count yourself in and join Jug Bay on a lantern-lit trail, animal displays, campfires, s'mores, hayrides, and crafts. Bring a flashlight and wear your costume! All ages welcome! 👻

 

  1. Napoli (Annapolis) | October 26 

Catch Ballet Theatre of Maryland’s Napoli from October 25-27 at Maryland Hall for the Arts! This charming and demure ballet features a brave fisherman and his love, a perfect treat for the whole family! 🩰 

 

  1. DrinkMaryland: Glen Burnie (Glen Burnie) | October26) 

Let the samples lead the way at DrinkMaryland, an open-air market where you can meet local artisans and dive into the Maryland craft beverage scene! Sample wines, beers, and spirits directly from the wineries, breweries, and distilleries. Admission is free, but tasting passes can be purchased in advance. Cheers!🍺 

 

  1. Candlelight Open Air: A Haunted Evening of Halloween Classics (Annapolis) | October 31 

Experience Candlelight Open Air concerts in Annapolis! Enjoy spooky Halloween-inspired music at the Annapolis Waterfront Hotel, all under the enchanting glow of candlelight. Tickets available now! 🕯️ 

 

  1. Friday Happy Hour at the Vineyards at Dodon (Davidsonville) | Recurring weekly on Fridays 

Cozy fall evenings at Dodon Vineyard’s Friday Night Happy Hour are a must! Reserve a spot at the pavilion and sip on delicious Dodon wines by the glass, flight, or bottle. 🍇 

 

lights strung across a city street with a historic church in the background at night
Image courtesy of Brandi McKeating.

 

Plan Ahead of the Holiday Rush

And if you love us in the fall, just wait until Winter in Annapolis.

 

  1. Fall Foliage Hike at SERC (Galesville) | November 2 

The beauty of fall is here at Scenic Rivers Land Trust’s Fall Hike! Enjoy stunning views and autumn colors, plus tasty treats. Space is limited, so register in advance for this free event!  

 

  1. Bay Bridge Run (Chesapeake Bay) | November 10 

Run, don’t walk—actually you can do both to your only chance at crossing the iconic Chesapeake Bay Bridge! The Bay Bridge Run is a 10K race that traverses the eastbound span of the Chesapeake Bay Bridge from Anne Arundel County to Kent Island in Queen Anne's County and finishes with a huge post-race party! 🌉 

 

  1.  Lights on the Bay (Sandy Point State Park) | November 23-January 1  

There's no better way to get the whole family into the holiday spirit than cruising along the shore of the Chesapeake Bay during Lights On The Bay! Weather permitting, the electric wonderland will be on full display nightly. ⭐ 

 

  1. Midnight Madness (Annapolis) | December 5,12,19 

When the clock strikes 12—it's Midnight Madness! Midnight Madness is nothing without late-night shopping in walkable downtown Annapolis with select stores open until midnight, featuring holiday treats, exclusive discounts, and festive displays. Don't miss out on your midnight haul! 🛍️ 

 

  1. Eastport Yacht Club Lights Parade (Eastport) | December 14 

Immerse yourself in the historic holiday charm of Annapolis Harbor and Spa Creek at the Eastport Yacht Club’s Lights Parade! A Chesapeake holiday tradition, celebrated for over 40 years, invites you to experience the joy of festive gatherings aboard beautifully decked-out boats, each displaying its own unique merriment. 🎇 

View the link for more events and to plan your stay today!