Please wait..
Please wait..
08-October-2026 Plan Your Stay
October is one of the most exciting times to visit Annapolis, Maryland. Between two major boat shows, Navy football weekends, Homecoming, and the Maryland Renaissance Festival, there's plenty happening throughout the month.
Whether you're coming for a day at the boat show, cheering on the Midshipmen, reconnecting with Naval Academy friends, or making a weekend of the fall festivities, it's worth planning a little extra time to enjoy the Chesapeake Bay area.
And if you're looking for somewhere to stay near Annapolis, consider making Chesapeake Paradise your waterfront home base.
The Annapolis Powerboat Show brings boating enthusiasts to historic downtown Annapolis for four days of exploring boats, marine equipment, new technology, and everything connected with life on the water.
From smaller recreational boats to impressive motor yachts, there's plenty to explore, whether you're seriously shopping or simply love boating.
With so much to see, spending more than one day at the show can be worthwhile.
Planning tip: Downtown parking and traffic patterns change during the boat shows, so check the event's official parking and transportation information before heading out.
There's something special about Navy football in Annapolis. The Midshipmen host Tulsa at Navy-Marine Corps Memorial Stadium on Saturday, October 10, with kickoff scheduled for 3:30 p.m.
It's a great weekend for visiting Navy families, alumni, and football fans, especially with the Powerboat Show happening at the same time.
If you're traveling with family or friends, staying together in a waterfront vacation rental can be a comfortable alternative to booking several hotel rooms.
The Annapolis Sailboat Show is another highlight of the fall season, attracting sailors, boat owners, and people who simply love being around sailboats.
Historic Annapolis becomes a gathering place for the sailing community, with boats to tour, marine exhibitors, educational opportunities, and plenty of opportunities to explore downtown restaurants and shops.
Whether you're an experienced sailor or just beginning to explore the possibility of owning a boat, the show offers plenty to discover.
Navy Homecoming brings Naval Academy alumni, families, and friends back to Annapolis for a weekend of reunions, traditions, and Navy spirit.
This year's Homecoming football game is against North Texas, with kickoff scheduled for 3:30 p.m. at Navy-Marine Corps Memorial Stadium.
For alumni traveling with spouses, friends, or extended family, a vacation home offers a wonderful way to spend time together beyond the game itself.
A short trip outside Annapolis brings you to another beloved Maryland fall tradition: the Maryland Renaissance Festival in Crownsville.
The festival features costumed performers, artisan shops, entertainment, food, and a lively recreation of a 16th-century English village.
It's a fun outing for couples, families, and groups of friends, and an easy addition to a fall weekend exploring the Annapolis area.
Planning tip: Festival tickets are sold online for specific dates, and popular weekends can sell out. Purchase admission before making the trip.
If you love the activity of Annapolis but would rather spend your mornings and evenings overlooking the water, Chesapeake Paradise offers a different kind of home base.
Located in the Deale/Churchton area of Maryland, our peaceful, two-acre waterfront micro-resort is a short drive south of Annapolis.
We offer five unique accommodation options, ranging from intimate spaces for couples or solo travelers to larger waterfront homes for families and groups.
Depending on the stay you choose, you can enjoy beautiful water views, comfortable gathering spaces, fully equipped kitchens or kitchenettes, and outdoor places to sit and enjoy the changing sky.
Our waterfront amenities include a private property pier, kayaks, a canoe, a hot tub, and fire pits. Some outdoor amenities are shared among guests staying in different accommodations.
For guests who enjoy the outdoors, October can be a lovely time for watching the birds, enjoying a fire by the water, or taking in a colorful Chesapeake sunset.
And after a full day of walking around Annapolis, exploring boats, or cheering at a football game, it's nice to come back to a place where you can put your feet up and enjoy the view.
Chesapeake Paradise House: Our largest accommodation, with 6–7 bedrooms and 4 bathrooms, is a great option for extended families and groups traveling together.
Chesapeake Paradise LITE: A 4–5 bedroom, 3-bathroom option for families and groups who want plenty of room without booking the entire house.
Waterfront Wonder Cottage: A charming 3-bedroom, 2-bathroom waterfront home with a full kitchen, fireplace, and inviting spaces for spending time together.
Sky-Lit Flat + Solarium: A private upstairs apartment with skylights, a beautiful bath, and a window-filled solarium bedroom overlooking the water. A lovely choice for couples or a quiet getaway.
Sunrise Suite: A spacious king suite with a beautiful bathroom, private balcony, and wonderful water views.
Whichever brings you to Annapolis this October, there's a good chance we have a Chesapeake Paradise stay that fits the occasion.
October brings a wonderful mix of Annapolis traditions, boating, football, and fall celebrations. You might come for one special event and discover that the surrounding waterfront communities are worth exploring, too.
At Chesapeake Paradise, you can spend the day enjoying the festivities and return to the water, the trees, and a beautiful Chesapeake Bay sky.
Planning your October trip?
Explore our five unique waterfront stays, check availability for your dates, and see which Chesapeake Paradise accommodation is right for you.
Shawn
Online