A Holiday Season to Remember in Merry Madison, Indiana

There’s never been a better time to experience the magic of the season in historic Madison, Indiana. This year, our city invites locals and visitors alike to enjoy three signature holiday‐events that combine heritage, fun and firelight: the 43rd Annual Nights before Christmas Candlelight Tour of Homes, the inaugural Santa Express and Christmas Crawl aboard our brand-new Madison Trolley Line, and the Very Merry Madison Christmas Celebration.

Nights Before Christmas Candlelight Tour of Homes

This beloved tradition returns for its 43rd edition, inviting guests to step inside exquisitely decorated historic homes, public heritage sites and a local church - all located in Madison’s National Historic Landmark District.  Tour dates are Friday Nov 28 & Saturday Nov 29, and again Friday Dec 5 & Saturday Dec 6, 2025. Fridays run from 5 p.m.–9 p.m.; Saturdays from 3 p.m.–9 p.m.  Tickets are $35 for adults. Children ages 5-12 are only $5.  Expect warm, glowing lighting, period decor, costumed greeters, and the unique blend of architecture and holiday cheer that makes Madison stand out this time of year. Moreover, your participation supports Madison’s historic homes and local businesses: proceeds from the Candlelight Tour benefit the participating historic sites. 

Santa Express

For those ready to slip into holiday pajamas and go big on festive fun, the inaugural Santa Express offers a fresh signature ride. All aboard the Madison Trolley Line for a morning brunch plus a holiday craft and a meeting with the jolly man in red himself at The White Barn Venue.  Participants will enjoy a light brunch and cocoa bar, hands‐on crafts, meet & greet (and photo!) with Santa, then write a letter and receive a personalized reply in the mail - complete with a commemorative photo.  The event is set for Saturday Dec 13, 2025, from roughly 12:45 PM – 4:00PM with 1-hour time slots. Families looking for cozy, memorable holiday moments will want to reserve early. 

Christmas Crawl

Adults wanting a festive, spirited holiday‐outing will appreciate something new: the Christmas Crawl aboard the trolley. Think holiday‐movie inspired fun: costumes, drinks, stops at six local venues, and the ease of trolley transport between locations.  Your ticket includes a drink at each stop, a souvenir cup, and extra specials or discounts at each venue. Dress as your favorite holiday‐movie character for added fun. (21+ only.) It’s the perfect blend of adult holiday cheer + the convenience of the trolley ride. A great holiday night out to complement the family‐friendly daytime events.

The Very Merry Madison Christmas Celebration

Downtown Madison transforms into a holiday wonderland during the Very Merry Madison Christmas Celebration - a community-wide festival filled with music, shopping, lights, and laughter. From twinkling storefronts and pop-up entertainment to the scent of cocoa in the air, the event captures the timeless charm of the season.

The highlight, of course, is Madison’s annual Christmas Parade, when Santa himself arrives in town to spread cheer and officially kick off the Christmas season. Families line the streets to wave, smile, and welcome St. Nick as he makes his way to town - a tradition that marks the joyful start of the holiday festivities in Madison.

Why This Season is Special

This year’s holiday lineup brings together several very different experiences under one festive umbrella: the heritage charm of the Candlelight Tour, the family‐friendly magic of the Santa Express, and the grown‐up holiday adventure of the Christmas Crawl. Not to mention the holiday classic that is the Very Merry Madison Celebration. Each uses the historic backdrop of downtown Madison, the convenience of the Madison Trolley Line, and the community’s trademark holiday spirit.

Madison is ready to shine this holiday season - whether you’re touring candlelit homes, riding in your pajamas to brunch with Santa, or hopping from bar to bar in a holiday‐movie costume aboard the trolley. Mark your calendar, grab your tickets, and make memories in our merry little river town.

Photo Credits:

Santa in Parade: Samantha Turner

Trolley: Lilly Comp

House with antique car: Sarah Prasil