Chrsitmas in Olde Jonesborough: Holly Dolly Sip & Stroll

About this event

If you are looking for the charm of a real-life Christmas village, it is time to pack your bags for Tennessee’s Oldest Town. From November 27 through December 19, Historic Jonesborough transforms into a month-long winter wonderland. With its brick-lined streets, local boutiques, and calendar packed with festive events, “Christmas in Olde Jonesborough” is the ultimate holiday road trip destination.

Whether you are looking for a romantic weekend of shopping and lights, a family getaway, or a trip with your furry best friend, here is how to plan your perfect holiday escape.

Kickoff Weekend: Dolly, Lights, and Whoville Magic (Nov 27 – Nov 28)

Start your holiday season with a healthy dose of Southern charm on Friday, November 27. The festivities begin at 4 p.m. with the Holly Dolly Sip & Stroll. You can wander through Downtown Jonesborough visiting over ten treat stops passing out Dolly Parton-themed goodies while checking off your gift list at locally-owned boutiques.

At 6 p.m., make your way to the Washington County Courthouse for the annual Lighting of the Christmas Tree. After a Washington county-wide children’s choir and a special Christmas story from local performer Paul Harris, the town goes completely dark. Families light individual candles in the quiet anticipation before the town’s massive 60-foot Frasier Fir bursts into light.

Sleep in on Saturday, November 28, before stepping right into Dr. Seuss’s imagination for the Whoville Christmas celebration from 11 a.m. to 3 p.m. Meet the Grinch at the historic Christopher Taylor Cabin, snack on “green treats,” and watch the Cheermeister Contest at 1 p.m. in front of the Courthouse. Since it is also Small Business Saturday, browse handmade artisan gifts at the Christmas Marketplace on the International Storytelling Center Plaza, and take advantage of free downtown gift wrapping.

For the Furry Family Members: A Doggone Christmas (Dec 5)

If your dog owns an ugly Christmas sweater, December 5 is your weekend to visit. From 11 a.m. to 3 p.m., Jonesborough hosts A Doggone Christmas. The first 50 visitors snag a free custom pet bandana at the Courthouse information tent before the 1 p.m. Costume Contest kicks off. Categories include Best Holiday Costume, Ugliest Christmas Sweater, and Pet/Owner Lookalike.

After the contest, parade your pup down Main Street and get their photo taken with Santa in his sleigh. Bring a pet donation for the Appalachian Highlands Humane Society to receive a handmade dog treat and a raffle entry. You can even warm up with a hot drink at the Jonesborough Paws in Blue tent, where proceeds support local K9 programs.

The Ultimate Family Getaway: Santa’s Christmas Village & Parade (Dec 12)

For families with young children, December 12 is the weekend to circle on the calendar. Head to the Jonesborough Visitors Center between 11 a.m. and 3 p.m. for Santa’s Christmas Village. Kids get the thrill of buying their own presents for family and friends at the Santa Mart, where every single item is just $1.

While you take advantage of the free gift wrapping by the David Crockett Civinettes, the kids can make free crafts and gift tags at Frosty’s Top Shop. Once you’ve snapped a photo with Santa by the Courthouse, grab dinner at a local food truck or downtown restaurant and claim your spot on the sidewalk. At 6 p.m., the spectacular Lighted Christmas Parade rolls through the historic district from Boone Street to Main Street.

A Classic Appalachian Finale: The Church Stroll (Dec 19)

If you prefer a slower, more reflective holiday experience, the final weekend offers a beautiful step back in time. On December 19 from 11 a.m. to 3 p.m., the Church Stroll invites visitors into the historic churches scattered throughout downtown. You will be treated to live seasonal music, historic tours, and festive treats. It is also your final chance to browse the Christmas Marketplace for last-minute artisan gifts while Santa makes one last sweep of the Courthouse to collect lingering wish lists.

Trip Planning Tips & Ongoing Magic

Throughout the entire festival, you can enjoy free gift wrapping on downtown purchases, live street music, and seasonal eats. If you are bringing kids, have them write a letter to Santa with a return address and drop it in the North Pole Mailbox beside the Courthouse by December 16.

To map out your itinerary, register for contests, or grab tickets for the Holly Dolly Sip & Stroll, head over to JBOChristmas.com or call 423-753-1010.

Don’t Forget Santa’s Mailbox!

Throughout the series, Santa’s official North Pole Mailbox is located beside the Courthouse. Drop off letters by December 17 with a return address to guarantee a personal reply from Santa before Christmas Day!

Celebrate the joy, community, and timeless charm of the season in Historic Jonesborough. It’s your perfect Northeast Tennessee Christmas destination!

For complete details on all events, visit JBOChristmas.com or call 423.753.1010.

From Jonesborough