Spend the Holidays in Delaware’s Quaint Villages

Spend the Holidays with a quaint visit to Kent County, Delaware. Fall into the spirit of the season with twinkling lights, home-made cookies and baked goods, a visit from Santa and friends, tax-free shopping, children’s activities, night-time parades, caroling, tree-lighting and more this year in Delaware’s Quaint Villages.

Kick off the holiday season by celebrating Small Business Saturday on November 30th. Help support small local businesses throughout Kent County by shopping at boutiques, antique & vintage stores, art studios, restaurants, coffee shops and more this Holiday season. Make plans and head to downtown Milford for Small Business Saturday and Santa’s Arrival event. Stop in the Santa House on Walnut Street for a free picture with Santa, candy canes and a stocking filled with candy! Or head to Dover’s Shop Small Business Saturday & Marketplace in downtown historic Dover. Come out to enjoy tax-free shopping and dine at local eateries. There will be specials, extended hours, kid activities, sidewalk sales, food trucks, entertainment and more!

 Join the fun this Holiday season with Capital Holiday Celebration on December 5th in downtown Historic Dover. Enjoy hot cocoa, caroling, Santa and tree lighting - all happening on Loockerman Street! Be sure to come back and enjoy the Light Up The Holidays Marketplace & Parade in downtown Historic Dover on Saturday, December 14th. Bundle up and watch the light-up, nighttime parade with decorative floats – you do not want to miss the fun!

Say hello to Santa at the Santa House along the Riverfront of the Mispillion River in downtown Milford during the 14th Annual Holiday Stroll on December 6th starting at 5pm. Enjoy local entertainment, wagon rides, strolling carolers, entertainment and more.

Step into an 1890s Victorian era setting at Delaware Agricultural Museum & Villages’ Farmer’s Christmas on December 7th. Stroll down the “avenue of trees” and make plans to see Santa & Mrs. Claus. Soak in the Holiday sights and smells with traditional Christmas carolers, fresh baked cookies, shopping and more.

Indulge into festive treats, a kids-only Holiday gift store, choral student groups and more at The Biggs Museum of American Art’s Happy Holidays Dover: The Biggs Museum’s Annual Holiday Event. Don’t miss out on this free family-friendly event everyone can enjoy on December 7th in Downtown Dover.

Get into the Holiday spirit with free hot apple cider, farm tours, and much more at Fifer Orchards & Country Store’s annual event, Cider Fest. Join in with this family-friendly festival each Saturday starting November 30th- December 14th. Stock up on fresh fruits & veggies, apple cider donuts, and locally made products at the Country Store. Top off the day with roasting marshmallows by the campfire and find your perfect Christmas tree, festive décor and uniquely decorated wreaths to take home with you!

Grab the family and catch the classic “Elf the Musical” at the Riverfront Theater in downtown Milford produced by Second Street Players.  Spread Christmas cheer and join in on the fun and laughter Fridays, November 29th, December 6th and December 13th. Saturdays: November 30th, December 7th, December 14th and Sundays: December 1st, December 8th, and December 15th.  

Enjoy cherished hometown community traditions by heading to the quaint villages of Clayton and Harrington for their annual tree lighting ceremony and nighttime parade with a special visit from Santa & Mrs. Claus on Sunday, December 1st during Christmas in Clayton 2019.  Or head to the Norman Barlow Pavilion on Tuesday,  December 3rd in the village of Harrington for the annual tree lighting and caroling event. This year’s nighttime Christmas parade for downtown Harrington is scheduled for December 6th – watch as Holiday themed floats topped with twinkling lights and a visit from Santa make their way through downtown Harrington.

Every fall & winter season, Ronny’s Garden World in Smyrna transforms into a sparkly themed Christmas Wonderland with lighted Christmas themed tree displays, indoor and outdoor holiday decorations, train set displays and more. 

Make memories and new traditions this holiday season by planning a trip to Kent County, Delaware. Explore our Villages and bring the whole family for a Holiday winter getaway to Delaware’s Quaint Villages. For a full list of events & festivals in Kent County, click here.

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