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As the summer’s heat fades into the cool breeze of autumn, Talbot County on the Eastern Shore of Maryland comes alive with events worth the drive. Here are 12 reasons to cross the bridge and get away for the day or the weekend.
1. Monty Alexander Jazz Festival
Head to the Shore for a weekend of jazz on the Bay. The sixth annual four-day festival kicks off with the musical stylings of Grammy nominated jazz vocalist René Marie at the Avalon Theatre, followed by a schedule of performances by Monty Alexander and friends. September 3-6; chesapeakechambermusic.org
2. First Weekend Art Walks
On the first Friday of every month, the art galleries of Easton—the cultural epicenter of the Eastern Shore—leave their doors open a little later for a casual evening of art appreciation. Be the first to check out new exhibits, meet and greet with gallery owners over a few light bites, and sip a little wine as you saunter through the nearly dozen galleries and shops downtown. September 4, October 2, and November 6; discovereaston.com
3. Charity Boat Auction
The Chesapeake Bay Maritime Museum’s 18th Annual Boat Auction takes place this weekend, with a flea market-style sale of boating and fishing gear, barbecue, and the big auction—featuring more than 100 boats from sailing dinghies to cabin cruisers. If you’re looking for a great deal on a used boat for a good cause, look to St. Michaels this Saturday. September 5; 8 a.m.; cbmm.org
4. Chesapeake Film Festival
Cinephiles unite! For three days, “watch, think, discuss,” more than two dozen full-length movies and short films in Easton. The three-day festival kicks off with a reception and two screenings on Friday, and culminates in a roast at the Bartlett Pear with wine on the patio on Sunday. September 18-20; chesapeakefilmfestival.com
5. Airport Day
Tap into your innermost aviator at Easton Airport for a day of family-friendly aerospace activities. Catch a formation flyover and watch the world-famous rubber chicken drop (yes, it’s a thing, and no, you don’t want to miss it). September 26; eastonairportday.com
6. Frederick Douglass Day
Celebrate the life and legacy of Talbot County’s famous native son, in the birthplace of one of America’s most prominent champions of justice and social reform, as downtown Easton hosts a commemorative parade, storytelling, inspirational readings, a family scavenger hunt, live music, and food and craft vendors. September 26; frederickdouglassday.com
7. The 33rd Annual Mid-Atlantic Small Craft Festival & Maritime Model Expo
Each year, boat builders and enthusiasts flock to this event at the Chesapeake Bay Maritime Museum. During the two-day festival, visitors can check out handmade works, put their skills to the test with hands-on workshops, and explore new museum exhibits. Highlights include live music, a small craft race on the Miles River, and cruises aboard a 1920 buyboat. October 3-4; cbmm.org/events
8. 7th Annual Picket Fences Around Oxford
Each year in May, picket fences hand-painted by local artists are erected around the town of Oxford, where they’re left on display for months before being auctioned off for charity in October. With the auction approaching, time is ticking to check out the picket fenced-landscape via the tour map, on foot or by bike. Explore the town’s unique local art, then bid on your favorite piece for a good cause. October 10; 4-6 p.m.
9. The 2015 Academy Art Museum Craft Show: “Blown Away”
The Academy Art Museum in Easton is home to the most prestigious juried craft show on the Shore, and this year’s theme—maybe our favorite yet—features a blown glass exhibit and glass blowing demonstrations. Take home an artisan piece, and your little artist’s own design—the kids’ craft workshop gives children a permanent keepsake—and check out the preceding special events (like the Riedel Glass Tasting) for more opportunities to explore the art. October 17-19; academycraftshow.org
10. Tilghman Island Day
A hideaway on the southernmost top of Talbot County, the maritime mecca of Tilghman Island is everything you’d want it to be—and the town’s official holiday showcases the best. Shuck an oyster, pick a crab (or two or 10), and then sit back and enjoy live music, the docking contest, and a host of local vendors before bidding in the live auction. Presented by the volunteer fire department, Tilghman Island Day is a celebration of life on a small Chesapeake Bay island. October 17; tilghmanmd.com
11. OysterFest
Hosted by the Chesapeake Bay Maritime Museum—which celebrates its 50th anniversary this year—OysterFest is “a celebration of the Chesapeake’s favorite bivalve,” featuring two stages of live music, an oyster stew cook-off, local fare (including oysters prepared in every way you can imagine), warm apple cider, cold beer, cooking demonstrations, and more. Don your best Halloween costume for the contest. October 31; cbmm.org/events
12. Waterfowl Festival
Perhaps Talbot County’s most highly anticipated event of the year, the internationally renowned Waterfowl Festival in Easton celebrates its 45th anniversary this year. Showcasing the sporting and hunting traditions of the Eastern Shore, the weekend-long festival includes calling contests, retriever demonstrations, and a canine aquatics competition. Art enthusiasts will enjoy gallery events and exhibits, and wildlife photography; children’s activities abound; and of age attendees can imbibe in the beer and wine pavilion, all in the name of conservation. November 13-15; waterfowlfestival.org