Festivals in Delaware’s Quaint Villages You Do Not Want to Miss!

Festival season kicks off next month in Delaware’s Quaint Villages! Now is the time to plan your excursion and head to one of the many events & festivals in Kent County. Our broad range of annual affairs include themes such as Delaware bay oysters, libations, history and culture, pirates, ladybugs, fireworks, peaches, Amish Countryside, live entertainment, concerts, food competitions, amusement rides and more!


Delaware State Fair

For over 100 years, the Delaware State Fair returns for 10 days of family-friendly fun, carnival rides, games, educational programs, exhibits, competitions, livestock, vendors, demonstrations,  and more. The annual fair highlights the heritage of the community and its ties to agriculture industry and businesses throughout the local community. This year’s fair marks the 101st anniversary over July 23rd- August 1st, 2020.


Amish Country Bike Tour

Enjoy a bike tour around Kent County’s thriving Amish countryside during the annual Amish Country Bike Tour. Register for this one-of-a-kind cycling experience – chose from various routes covering 15, 25, 50, 75 or 100 miles of terrain just west of Dover. Stops are provided along the way with healthy snacks and hydration drinks. Don’t forget the best stop – the Amish pie stop! At the finish line, all cyclists receive a hot catered meal! This annual cycling event takes place the Saturday after Labor Day.  This year’s Annual Amish Country Bike Tour is celebrating their 34th year on Saturday, September 12th, 2020. 

Fifer Orchards Fall Festivals

Saturday, September 26th, 2020 kicks off fall weekend fun at Fifer Orchards Fall Festival. Come for family-friendly farm fun with tractor trains, food vendors, live music, six-acre themed corn maze, super straw slides, pumpkin jumping pad and more! Fall Festival Saturdays at Fifer Orchards & Country Store start Saturday, September 26th, 2020 and run through October 31st, 2020 from 10am-5pm. Don’t forget to purchase a few pumpkins while you’re there!.


Leipsic Oyster Festival

Every October, the quaint village of Leipsic plays host to the Annual Leipsic Oyster Fest. Experience an afternoon filled with fresh and fried Delaware Bay oysters, burgers, steamed crabs, local craft beer options, entertainment, and family-fun activities.

For over 42 years, June Jam Music Festival has been rockin’ out at G&R Campground in Houston, Delaware. Over the years, June Jam has hosted national headliners along with East Coast touring bands and local musicians.  The 42nd Annual June Jam will be held on Saturday, August, 15th. Musicians and entertainment include Jason Morton and the Chesapeake Sons, Hotwire Reunion, Tenfold Trouble, and Petting Hendrix, to name a few.

Bowers Beach Heritage Weekend

Experience Bowers Beach heritage and history like no other during Bowers Heritage Weekend on October 10th, 2020 and October 11th, 2020. This two-day event kicks off Saturday with Knap-in and food trucks. Sunday, October 11th starts with a 5k run/walk, Lenape tribe of Delaware with drummers and dancer, indigenous food sampling, primitive skills, demonstrations, fresh Delaware Bay oysters, local archaeologists and more!


18th Century Market Fair

Living history comes alive the first Saturday in November in downtown Historic Dover at the 18th Century Market Fair. Watch as woodworkers, weavers, blacksmiths and other artisans craft demonstrations display their skills on Dover’s Historic Green. This rain or shine event is free fun for the entire family – enjoy live entertainment, food and drink, vendors and more! This year’s event is Saturday, November 7th, 2020.

Fifer Orchards Cider Fest

Every Saturday from November 28th until December 12th, 2020, Fifer Orchards & Country Store hosts Cider Fest Saturdays. Start a new holiday tradition and find your next Christmas tree at Fifer’s while roasting marshmallows by the bonfire and sipping on hot apple cider. Stop in the Country Store for all your local seasonal favorites – including local honey, apple butter, apple cider donuts, meats, eggs, and more! 

Small Business Saturday

Small Business Saturday starts on November 28th, 2020. Spend the day tax – free shopping while supporting local community businesses. Head to downtown Dover for all day activities including food trucks, children’s activities, entertainment, crafts, vendors and more. Next, head to downtown Milford to visit Santa at the Santa House all while shopping and dining at various establishments in Milford.


Capital Holiday Celebration

Get into the Holiday spirit in Downtown Dover with the Capital Holiday Celebration. Enjoy vendors, food trucks, caroling, annual tree-lighting ceremony and more. This is a true celebration in the heart of the capital of the First State, make new holiday memories in Delaware’s Quaint Villages. This year’s annual Capital Holiday Celebration is on Thursday, December 3rd, 2020 from 5pm-8pm.  

Light up the Holidays Parade & Marketplace

Spend the evening in downtown Dover with Light up the Holidays Marketplace & Parade. Come for family fun for everyone to enjoy. Attend the annual night-time parade, visit with Santa, and lighted decorative floats, marching bands and more!

Milford Holiday Stroll

Milford Holiday Stroll is a great family-friendly event in downtown Milford. This year’s Holiday Stroll is on Saturday, December 4th, 2020. This event includes local entertainment, visit with Santa Claus at the Santa House, wagon rides, caroling, refreshments and more!   

For a full list of events & festivals in Kent County - check out our event calendar on our site!

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