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.


Wyoming Peach Festival

For a day filled with peaches, desserts, contests, kid’s activities, entertainment, bounce house village and more, make plans to attend the 30th Annual Peach Festival in Wyoming, Delaware. This year’s celebration of peaches takes place Saturday, August 1st, 2020 from 9am-3pm. The Peach Festival kicks off with the annual parade and follows with a full day of festivities for families to enjoy.

Fifer Orchards Peach Ice Cream Day

Spend the afternoon at Fifer Orchards & Country Store in Camden for Customer Appreciation Day on Saturday, August 8th, 2020 for a complimentary peach ice cream cone, kid’s activities, tractor train rides, farm tours – and even pick your own peaches! Be sure to make plans this year and attend Fifer Orchards Peach Ice Cream Day for a peachy family-gathering.

June Jam

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.

Harrington Heritage Days

The village of Harrington plays host to the Annual Harrington Heritage Days – a true celebration commemorating Harrington’s rich history. Spend the day learning about Harrington’s culture, enjoying food and demonstrations, a parade, live entertainment and children’s activities. This year, Harrington Heritage Days is celebrating their 42nd year on Saturday, August 29th, 2020 from 9am-4pm.

Dover Comic Con

Dover Comic Con is an annual free event for all ages embracing pop-culture through comics, movies, anime and cosplay. Come for the vendors, fan groups, activities, food tucks, indoor and outdoor market, artists and more. This event takes place every August in downtown Dover. The 8th Annual Dover Comic Con takes place on Saturday, August 15th, 2020 starting at 10am.


Feel the speed at Dover International Speedway when NASCAR comes back to town on Friday, August 21st, 2020 to Sunday, August 23rd, 2020. Start your engines with the “General Tire 125” ARCA Menards Series East race at 5pm. On Saturday, stick around for the NASCAR XFINITY Series Race at 4pm. Wrap up the weekend with “Drydene 400” NASCAR Cup Series Race on Sunday at 3pm. In between races make a stop at the FanZone for vendors, food options, children activities and more.


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. 

Riverwalk “Freedom” Festival

Attend the 20th Anniversary of Riverwalk “Freedom” Festival in downtown Milford on Saturday, September 19th, 2020. Spend the day in downtown Milford with all-day activities starting at 9am including crafts, vendors, kid’s corner, car show, duck dash, food trucks, live music and a Beer garden.  Stick around after dusk for a spectacular firework display over the Mispillion River.

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.

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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