September in Queen Anne’s County: 10 Ways to Make the Most of Early Fall
September in Queen Anne’s County!
Summer may be winding down, but September is one of the best times to experience Queen Anne’s County. The crowds begin to thin, the temperatures cool, and the Chesapeake Bay takes on a whole new rhythm as we ease into fall.
From waterfront dining and local markets to historic sites, scenic trails, craft beverages, and time on the water, September offers plenty of reasons to make a trip to Maryland’s Eastern Shore. Whether you’re planning a day trip, a weekend getaway, or looking for something new close to home, Queen Anne’s County has plenty to explore.
Here are 10 ways to enjoy Queen Anne’s County this September!
- Explore the Outdoors: Take advantage of the cooler temperatures and explore Queen Anne’s County’s trails, parks, and natural areas. Walk through scenic landscapes, spot local wildlife, or simply enjoy a peaceful afternoon along the water. Cross Island Trail, South Island Trail, and Wye Island Natural Resource Management Area are just a few places to get outside.
- DOCK, DINE & Enjoy the last tastes of Summer: September is the perfect time for one more waterfront meal before fall arrives. Grab a table overlooking the Chesapeake Bay, order a plate of steamed crabs, and pair it with a refreshing crush. From dock bars to waterfront restaurants, Crabs n’ Crushes is still in season!Enjoy local seafood, live music, beautiful sunsets, and those classic Chesapeake views while you can.
- Shop Local at the Farmers Markets! September means fresh produce, local products, baked goods, handmade treasures, and plenty of reasons to shop small. Stop by the Centreville Farmers Market or Kent Island Farmers Market and meet some of the local farmers, makers, and vendors who make Queen Anne’s County special. Find local Markets and upcoming events!
- Experience Chesapeake “Boat to Table” Dining: You can’t visit the Eastern Shore without enjoying fresh seafood! Queen Anne’s County’s waterfront restaurants offer plenty of opportunities to enjoy local flavors with a view.Order Maryland favorites, dig into fresh catch, or try something new while taking in the scenery of the Chesapeake Bay & surrounding waterways.
- Go Birdwatching & Get Back to Nature: As the seasons begin to change, September is a beautiful time for birdwatching and exploring Queen Anne’s County’s natural areas. Visit the Chesapeake Bay Environmental Center, explore Ferry Point Park and Trail, or find a quiet spot along the water and see what wildlife you can discover.Bring your binoculars, take your time, and enjoy the slower pace of early fall on the Eastern Shore.
- Discover Local Shops & Small Businesses! Make a day of it and shop small throughout Queen Anne’s County. From unique gifts and local art to antiques, specialty products, and locally made goods, you never know what you’ll find when you step inside a locally owned business.Take a stroll through historic downtown Stevensville or Centreville and make a few local stops along the way.
- Get out on the water: The summer season may be winding down, but there’s still plenty of time to enjoy the Chesapeake Bay. Book a fishing charter, sunset cruise, leisure cruise, or boating adventure and experience Queen Anne’s County from the water.Prefer to explore on your own? Look into kayak and stand-up paddleboard rentals and make your own adventure at Kent Point Marina
- Sip your way through Queen Anne’s County:
September is a great month to Sip & Savor your way around the county. Visit local wineries, breweries, and craft beverage makers to sample Maryland-made beer, wine, and spirits while enjoying the scenery.
Looking for something to put on your fall calendar? Keep an eye out for Shore Pours events and experiences featuring Queen Anne’s County’s local craft beverage scene. Discover Craft Made in Queen Anne’s County!
- Step Into Local History! September is a great time to slow down and explore the stories that shaped Queen Anne’s County. Visit historic downtown Stevensville and downtown Centreville, where you can discover historic buildings, local museums, and special events throughout the year.
And don’t miss First Saturdays, when historic sites in Stevensville open their doors for tours and special programming.
With Maryland’s 250th anniversary celebrations continuing throughout 2026, there are even more opportunities this year to connect with the history of Queen Anne’s County and the story of Maryland. Explore Maryland 250 events and history in Queen Anne’s County
- Make it a Getaway! Why make it a day trip when you can stay awhile?Turn your September adventure into a weekend getaway at one of Queen Anne’s County’s hotels, resorts, inns, or bed & breakfasts. Spend the day exploring, enjoy dinner by the water, catch a sunset, and wake up ready for another day on the Eastern Shore. Come for the Bay. Stay for the experience. And leave already planning your next visit.
Spotlight Events:
09/05/2026 Paint Plein Air
Godfrey’s Summer Concert Series
Live Music at Chesapeake Manor Vineyard
09/05/2026 Queen Anne’s County Historic Sites First Saturday
09/06/2026 Tranzfusion playing at Love Point Vineyards and Winery
09/12-13/2026 4th Annual Kent Island Pickleball Tournament
09/13/2026 Kids Markets @ Cult Classic
09/19/2026 MORE Revolutionary Spirits: Distilling The Revolution
09/19/2026 Eastern Shore Street Machines 1st Annual Car Show
09/25-27/2026 Concours d’Elegance
09/26/2026 Let Freedom Ring: A Revolutionary Birthday Bash! Downtown Centreville
These are only a few of the amazing events we have going on during the month of September here in Queen Anne’s County! To find more, visit our events page here!
Ready to Explore?
September is your invitation to experience a different side of Queen Anne’s County — cooler days, beautiful waterfront views, local flavors, historic charm, and plenty of ways to enjoy the outdoors.
Plan your September getaway and discover what’s happening in Queen Anne’s County!
Explore upcoming events and start planning your visit.
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