Fall Festivals and Events Near Kent Island

Fall is here and what could be more fun then heading out for Fall Festivals and Events Near Kent Island. We’ve rounded up a list of fun happenings through October and we will be adding to it as we find more! In the meantime, call your friends, get out your calendar and plan your Fall Fun on Kent Island! Click the links for details.


Eat, Drink & Be MARRIED!

WHEN: September 16, 2023 @ 12:00 pm – 3:00 pm
WHERE: Emily’s Produce
2214 Church Creek Rd. Cambridge
This is the last weekend that our own Emily will spend here at the market as a ‘Jackson girl’ and we want to make it the most memorable day yet! There will be wedding cake, specialty cocktails, live music (Good Times Entertainment), passed apps, and plenty of time to celebrate our bride to be.

Fall Bingo for Chesapeake Cats and Dogs

When: September 17th, 2023
Where: Kent Island American Legion Post 278
Get your tickets now for CCAD’s Fall Bingo! Happening on Sunday, September 17 at the American Legion Post 278 in Stevensville MD. Doors open at noon, bingo starts at 2pm and usually lasts until around 5pm.

Prizes are designer bags and baskets that are filled with other goodies! There will also be raffles, Chinese auction, and a couple of local vendors. Bring your appetite, too, for our bake sale table and our food counter! Tickets are available now on our website! $40 if you purchase in advance, $45 at the door.https://www.chesapeakecatsanddogs.org/ 

Chestertown Fall Fun Fest

When: September 23, 2023
Where: 200 High Street, Chestertown
Fall FunFest will feature a free, festive, carnival-style midway with games and prizes hosted by local businesses and organizations. Beer, wine, cocktails, popcorn and fun for all ages. Live music by the Blues-Keepers Band!


Annapolis Baygrass Festival

When: September 30 – October 1, 2023
Where: Sandy Point State Park 1100 E. Collge Parkway, Annapolis, MD
The Annapolis Baygrass Music Festival is a conservation-focused musical event where just by having fun you’re helping to Save the Chesapeake Bay. Baygrass blends the finest progressive bluegrass music with a gorgeous beachfront venue and a core mission to protect and restore the Bay. You’ll enjoy 14 top touring bands on 2 stages over 2 days, delicious local food, microbrews, wines, craft cocktails/mocktails, workshops, craft vendors, and fun activities for all ages. Learn More

Chesapeake Film Festival

LIVE FESTIVAL Sept 30 – Oct 1, 2023
VIRTUAL FESTIVAL Oct 2 – Oct 8, 2023
Founded in 2008, it is the mission of the Chesapeake Film Festival to entertain, empower, educate and inspire diverse audiences of all ages by presenting exceptional independent films and events. We offer outstanding filmmakers, experienced and emerging, a forum to showcase and discuss stories of compelling interest to our local and global community. Because of our location on the Chesapeake Bay and our diverse population, we prioritize films that focus on the environment and social justice issues. The Festival also strives to be an economic engine for the Eastern Shore by enticing visitors to experience exceptional films, world-famous seafood, art, and the beauty of our waterways.

3rd Annual Mystic Market

When: October 1st, 2023
Where: 222 Shopping Center Rd, Stevensville
3rd Annual Mystic Market at Foundations Island Yoga! Free Entry, Over 40 Vendors…All things Metaphysical & Holistic, Readings,Healings,Crystals,Crafts,Food Trucks & More

Mid-Atlantic Small Craft Festival

When: October 6-8, 2023
Where: Chesapeake Bay Maritime Musuem
CBMM hosts Mid-Atlantic Small Craft Festival XXXX on Friday-Sunday, Oct. 6-8, welcoming one of the nation’s largest gatherings of small boat enthusiasts and unique watercraft back to its waterfront campus. Hundreds of amateur and professional boatbuilders and enthusiasts will come from all over the region to display their one-of-a-kind kayaks, canoes, and other traditional small craft at the 40th edition of the annual festival, which runs 10am–5pm all three days. Click HERE to learn more.

Artoberfest Historic Stevensville

When: October 7th, 2023
Where: 415 Love Point Road, Stevensville
Join us for the annual ARTOBERFEST on October 7th from 10am to 4pm in downtown Historic Stevensville Arts & Entertainment District. The streets will be closed down and filled with handmade artisans and crafters, live music, DJ, performers, kids art activities, food, a Beer & Spirits Garden for adults and Root Beer Floats for the kiddos. There will be a balloonist, face painting, Fairy Strands and pumpkin decorating for kids as well as a Corn Hole Tournament for adults!
For more information on sponsorship or vendor opportunities and ways that you can volunteer at this event… call 410-604-2100. Rain Date-Sunday, October 8th. 

Farm Charm’s Fall Celebration Event

When: October 7th, 2023
Where: Farm Charm 106 Outlet Center Drive, Queenstown
It’s that time of year again when the leaves are falling and pumpkin spice is in style. Please come celebrate with Farm Charm and find some awesome Fall decorations and candles for your cozy home. Spin the discount wheel with any purchase, find some great sale items, enjoy refreshments, and enter raffles with any purchase! We are excited to see you there! 

Easton Beer Fest

When: October 7th, 2023
Where: Easton Volunteer Fire Department, 315 Leonard Rieck Drive, Easton
SUPPORT LOCAL ~ DRINK LOCAL The 8th Annual Craft Beer Fest will be held on Saturday, October 7, 2023 from Noon to 4pm (VIP’s Enter at 11am). Maryland’s largest under cover craft beer festival will feature 40+ Breweries, Wineries and Distilleries will be pouring 120+ Craft Beers, Ciders, Seltzers, Wines & Spirits from the Mid-Atlantic region and beyond, with Live Music. Food, Vendors, Raffles and games of chance will be available. MUST BE 21+ TO Attend (ID required to enter)

Other Fun Festivals Nearby

Annapolis Boat Show October 5th – 8th

Good Beer Festival Salisbury October 13th & 14th

Ocean City SunFest October 19th – 23rd

We hope you get out and enjoy all these fall festivals and events near Kent Island this year! Hosting an event and would like to add it to our list? Email ilovekentisland@gmail.com to find out how!

I Love Kent Island

www.ILoveKentIsland.com is the premier online guide for locals and visitors alikeWe highlight the individuals, organizations, and events that make Kent Island a magnificent place to live, visit, and play. 

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