Events
Shipshewana Ice Festival
Bundle up and head downtown Shipshewana at 10AM sharp on Friday in January to see ice carvers in action. Twelve shops along the route will host talented artists as they transform massive blocks of ice into breathtaking works of art.
Afterward, plan to return for the Icy & Spicy Wings Competition at Smokehouse Grills & Supply on Morton Street, which also hosts the Chili Cook-Off on Saturday. For just $10, you can try eight wings, or pay $20 to sample every chili entry and help crown the winner.
For the full experience, purchase an Ice Festival Pin for $20 at the Shipshewana CVB or the Kitchen Cupboard in Davis Mercantile. The pin is your all-access pass: sample and vote on the best wing sauce, taste every chili and cast your vote, plus unlock special deals at more than 35 stores—worth over $100 in value.
The excitement wraps up with the Ice Carving Competition awards, announced Saturday at 4PM in the Davis Mercantile parking lot.
Shipshewana Pajama Days
Get up early and show up in your pajamas for another Shipshewana tradition held every February. Beginning at 5AM sharp, locally owned businesses kick off the day with their very best specials and first-round deals of the year.
For many, it’s more than just shopping—it’s a chance to gather with friends. “We’ve been coming for the last three-or-so years,” said Heather, a pajama-clad shopper from Fort Wayne. Another mom from Churubusco, shopping with her two daughters in matching red plaid pajamas, shared, “I’ve come with friends the last few years, but this year I brought the kiddos. It’s so much fun to see all the unique things on sale that you can’t find anywhere else.”
By sunrise, the sidewalks along Van Buren Street are filled with pajama-wearing shoppers strolling from storefront to storefront, while live local musicians add to the lively, festive atmosphere.
Ship-Chic Craft and Vintage Show
Visit us in March, October, and December when sellers from all over the Midwest descend on Shipshewana with gifts, vintage items, home decor, crafts, clothing, accessories, beauty products, jewelry, baked goods, signs and more; old stuff, new stuff and awesome stuff all picked with quality in mind.
Hosted by the Shipshewana Auction, artisans offering authentic handmade items include Clean Craft Soapworks, Hand in Hand Art, Handmade by Carol, B Honey, Black Dog Forge, Crafty Couple, Delightful Designs by Shirley, Scents by Joelle, Cow Creations, Feather and Vine, Red Apron Soap, and Rustic Creations.
The first 100 shoppers through the door get a reusable tote, and four lucky bags each have a $25 gift certificate that can be used at the show!
Mayfest
Each year we are excited to usher in the spring season with a Mayfest celebration in Shipshewana where locals and visitors alike participate in good ole’ fashioned hometown fun! The Grand Mayfest parade kicks things off downtown on Saturday morning, followed by band and choir concerts, kid’s activities, live entertainment, softball tournaments, food trucks, a benefit breakfast and much more!
Middlebury Summer Festival
Every year during the last week in June, the Middlebury, Indiana Chamber of Commerce hosts a Summer Festival with live Bluegrass and Gospel music, delicious festival fare, artisan crafts, children’s activities and the largest small-town parade in our area. Join us for a run through the community or, if that isn’t your speed, enjoy the new and exciting food vendors scattered throughout the festival, along with more than 35 local sponsoring businesses and organizations.
Pumpkinvine Classic Bike Event
Choose from four scenic routes through Northern Indiana’s rolling farmland when you take part in the Pumpkinvine Classic, now celebrating its 24th year in Amish Country. Riders depart from Das Dutchman Essenhaus between 8–9AM, with route options of 19, 40, or 63 miles.
After completing the ride, participants are rewarded with a hearty hot meal and a spread of delicious homemade pies, served from 11AM–4PM at the finish line.
The experience kicks off the night before—pick up your race packet at Das Dutchman Essenhaus on Friday evening and stay for the fireworks show. And when the ride is done, make the most of your weekend by checking out the local festivals happening throughout the area.
Middlebury Fall Festival
Every town has a festival that showcases its heritage and culture, and in Middlebury, that celebration is the Fall Festival.
The weekend kicks off Friday evening with a Pork Chop Dinner hosted by the Fire Department, followed by fireworks at Das Dutchman Essenhaus at dusk. On Saturday, the fun continues with local artisans and crafters displaying their work while visitors enjoy classic festival favorites—fried pies, ice cream, elephant ears, corn on the cob, kettle corn, and more. Many food booths are sponsored by the Music Parents Association, helping raise funds for local music programs.
Stock up on fall produce and flowers at the farmers market, test your skills in the cornhole tournament, or join the Donut Fun Run sponsored by Rise n’ Roll, with all proceeds benefiting the Middlebury Food Pantry. Perennial favorites also return each year, including Knight of Destruction Monster Truck Rides, live woodcarving, pottery, Amish artisans, ornamental gourds, and vibrant fall mums.
Visitors are encouraged to bring lawn chairs—or borrow one from the information booth—to easily enjoy the live music happening all weekend in the downtown parks. To round it out, downtown shops extend their hours, and nearly 50 local businesses and organizations will be on hand, making the Middlebury Fall Festival a true community celebration.
Autumn Adventures Annual Straw Bale Art Trail
From September 1 to November 2, take a scenic drive through Amish Country and discover festive fall sculptures at 39 different locations. Each piece is crafted from locally grown straw and brought to life with color and creativity by talented local artists.
Meet some of the trail’s most beloved characters—Louie the Bluey, Pete and Poppy the Donkey, Laverne the Steer, and WillHAY Nelson—along with many more whimsical creations. Tour the trail through Shipshewana, Howe, LaGrange, and Middlebury, snap photos, and share your favorites with #AutumnAdventure25. Don’t forget to cast your vote for the sculpture you love most!
This annual event is made possible with support from Arts United of Greater Fort Wayne, Inc. and the Indiana Arts Commission, which receives funding from the State of Indiana and the National Endowment for the Arts.
Middlebury Pumpkin Races
The annual Middlebury Pumpkin Race in Middlebury is a unique event. Pumpkins are decorated by participants, fitted with wheels and raced down the street to raise money for local non-profit organizations. The winner of the race determines the charity that receives the proceeds from the race. Various other prizes, such as fastest, most spirited, cutest, and most original pumpkins are also awarded.
Lights of Joy
Between Thanksgiving and New Years, hundreds of visitors make their way to Shipshewana to drive through an amazing experience of a more than 2 million LED Christmas light display, creating an almost two-mile symphony of colorful light scenes, animatronics and more. The route is lit between 6PM-9PM Sunday through Thursday and 6PM-10PM Friday and Saturday. Tune your radio to our Christmas music broadcast and soak in the holiday spirit!
