5 Ways to Explore Annapolis this October

With the leaves changing colors and a crisp breeze blowing through Annapolis, it’s clear October has arrived. Though we’re all upset summer has ended, the coming of October doesn’t mean that things slow down here in Annapolis. From fall festivals and two of the world’s largest in-water boat shows to haunted tours of the city and early holiday shopping, there’s still plenty ways to explore Annapolis in October. Here are five suggestions to keep you exploring in October:

Historic Haunting Tours

Founded in 1649, Annapolis carries with it a ton of history, which means a lot of ghostly tales of hauntings around town. Walk across the creaking floors of the most haunted mansion in Annapolis after dark…if you dare.  As the weather chills and dying leaves crunch under your feet, it’s time to experience a ghostly tour with Annapolis Tours by Watermark and Historic Annapolis. Led by a guide, you’ll wander the streets stopping by some of the most haunted buildings in town. During the month of October, Watermark’s Historic Ghost Walk includes an exclusive trip inside the historic Sands House (one of the oldest in Annapolis) at night. Ghoulish period-dressed guides lead the way by candlelight through historic – and many say haunted – Annapolis. Special Historic Hauntings tours will run Friday and Saturday evenings, from October 6th through October 26th. Click here for more information.

The U.S. Sail & Powerboat Shows

From October 5th through the 15th, City Dock and the Annapolis Harbor are transformed to accommodate two of the largest in-water boat shows on earth. From the 5th to the 9th, the U.S. Sailboat Show inundates the waterways, showcasing everything from the year’s most cutting-edge sailing vessels, to all the equipment a sailor could dream of. The U.S. Powerboat Show quickly replaces the sails at the floating docks from October 12th through the 15th. Both shows offer sailors and boaters the chance climb aboard their dream boats before stocking up on boating essentials at the dozens of vendor tents offering everything from navigational equipment to charter cruises. If you’re in the market for a boat, now’s your chance to discover what’s out there. Tickets are available for purchase in advance by clicking here, or at the gate during the shows.


With the holidays right around the corner, October is a great time to get a jump-start on your gift shopping. From art galleries and apparel to antiques shops and specialty boutiques, downtown Annapolis has a little of everything. Looking for that special little something with a twist of Chesapeake Bay? You’ll find it downtown. If you’re looking for a certain gift from a brand name store, head over to the Westfield Annapolis Mall or the Annapolis Towne Centre, where you’ll find all the big store names to get your early shopping knocked out. With the leaves changing colors around town, and the weather a comfortable temperature, Annapolis is a great place to take a day strolling the brick streets in search of gifts for the holidays. Find all the shopping options Annapolis has to offer by clicking here.

Explore South County

The Annapolis Countryside, or Southern Anne Arundel County (South County to locals), is the perfect place to embrace the spirit of fall with rolling hills and bay-side views. One way to get a Maryland fall experience is to stop by the Oyster Festival at the Captain Avery Museum (1418 East West Shady Side Road, Shady Side, MD 20764). Here, you’ll enjoy food, live music performed by local musicians, unique arts and crafts, face painting for the kids, and demonstrations showing the vital role oysters play in maintaining the health of the Chesapeake Bay. The event is held on October 15th from 12:30 PM to 5:00 PM.

After you’ve gotten your fill on oysters, head over to one of two great fall festivals held in South County each weekend throughout October.

Fall Festivals

The Greenstreet Gardens Fall Festival (391 West Bay Front Road, Lothian, MD 20711) and Homestead Gardens’ Annual Fall Festival (743 West Central Avenue, Davidsonville, MD 21035) are in full swing each weekend throughout the month of October, offering families everything from fun activities like corn mazes and hayrides to pumpkin carving/painting and fresh, seasonal vegetables. Rotating events keep things interesting each weekend, so there’s all the reason in the world to visit more than once through October!

Now get out there and explore Annapolis this October!


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