10 Most Fun Things To Do In Middlebury, Indiana

Middlebury, Indiana, is a quaint town in the heart of Amish County. The town is brimming with cultural heritage and contemporary charm and has a rich history dating back to the early 19th century.

Middlebury boasts a unique blend of Amish traditions and modern attractions that draw visitors from near and far. Each year, Middlebury attracts thousands of visitors eager to explore its picturesque landscapes and immerse themselves in Amish culture. 

From guided tours of Amish farms to leisurely strolls through quaint village shops, there’s something for everyone in this vibrant community.

Middlebury’s popularity as a tourist destination can be attributed to its authentic Amish experiences, including buggy rides, quilt gardens, and traditional cuisine. 

The town’s bustling events calendar, featuring festivals, concerts, and craft fairs, also adds to its allure, offering visitors a taste of local culture and hospitality.

The weather in Middlebury varies throughout the year, with warm summers perfect for outdoor activities and cozy winters ideal for exploring indoor attractions. 

The best time to visit Middlebury is during the spring and fall months when the weather is mild and the landscape bursts with vibrant colors.

Middlebury, Indiana, offers a perfect blend of old-world charm and modern amenities which makes it an unforgettable destination for travelers seeking an authentic Midwestern experience.

Whether you’re a local resident or a visitor passing through, there’s no shortage of fun activities to enjoy in this charming town. From exploring Amish culture to outdoor adventures, Middlebury has something for everyone. Here are the top 10 most fun things to do in Middlebury, Indiana.

1. My Amish Indiana

Start your journey with a guided tour through the picturesque countryside to learn about the rich traditions and way of life of the local Amish community. Experience the simplicity and craftsmanship of Amish culture as you visit farms, shops, and authentic homesteads.

My Amish Indiana

My Amish Indiana was established in 1991 and is a unique community founded by Amish families seeking a simpler way of life. They migrated from Indiana to Wyoming, bringing their traditional customs and values with them. 

The community, nestled in the scenic landscape of Middlebury, is a testament to their dedication to preserving their cultural heritage. 

Despite being far from their original roots, the Amish in My Amish Indiana continue to live a lifestyle characterized by simplicity, hard work, and close-knit community bonds. 

Visitors to the area can immerse themselves in Amish culture by exploring the community’s farms, shops, and homesteads. It’s a fascinating glimpse into a way of life that emphasizes family, faith, and a deep connection to the land.


13957 Adirondack Ct, Middlebury, IN 46540, United States

2. Essenhaus Village Shops

Indulge in a shopping spree at Essenhaus Village Shops, where you’ll find a delightful array of handcrafted goods, home décor, and locally made treats. Explore charming boutiques, artisanal shops, and quaint galleries, perfect for finding unique souvenirs and gifts.

Essenhaus Village Shops

The Essenhaus Village Shops were established in 1966 as part of the larger Essenhaus complex. This shopping area offers a variety of boutiques, artisanal shops, and galleries housed in charming, rustic buildings. 

The shops cater to both locals and visitors, showcasing a wide range of handcrafted goods, home décor items, and locally made treats. 

One interesting fact about the Essenhaus Village Shops is that they are located adjacent to the Das Dutchman Essenhaus, a renowned family-style restaurant serving authentic Amish cuisine. 

This proximity allows visitors to enjoy a full day of shopping and dining in one convenient location and enjoy some fun things to do in Middlebury.

Over the years, the Essenhaus Village Shops have become a popular destination for those seeking unique gifts, souvenirs, and treasures crafted with care by local artisans.


240 US-20, Middlebury, IN 46540, United States

3. Pumpkinvine Nature Trail

Get outdoors and explore the scenic beauty of Pumpkinvine Nature Trail. This 17-mile trail offers opportunities for hiking, biking, and birdwatching amidst lush greenery and tranquil landscapes. Pack a picnic and spend a leisurely day surrounded by nature.

Pumpkinvine Nature Trail

The Pumpkinvine Nature Trail was established in 1993 as a recreational trail for hiking, biking, and nature enthusiasts. It spans approximately 17 miles and winds through picturesque countryside, offering stunning views of lush greenery and tranquil landscapes. 

One interesting fact about the Pumpkinvine Nature Trail is that it follows the route of the historic Pumpkin Vine Railroad, which operated in the late 19th and early 20th centuries. 

Today, the trail provides a peaceful retreat for outdoor activities, with amenities such as picnic areas and rest stops along the way. It is a popular destination for locals and visitors alike, offering opportunities to explore nature and enjoy outdoor adventures year-round. 

Whether you’re looking for a leisurely stroll or a challenging bike ride, the Pumpkinvine Nature Trail offers something for everyone to enjoy amid the beauty of Indiana’s countryside.


Between Shipshewana & Middlebury, Middlebury, IN 46540, United States

4. Essenhaus Heritage Hall

Essenhaus Heritage Hall was established in 1985 as a part of the larger Essenhaus complex. This iconic building serves as a venue for various events and gatherings, including weddings, conferences, and community celebrations. 

Essenhaus Heritage Hall

One interesting fact about Essenhaus Heritage Hall is that it showcases traditional Amish craftsmanship and design with its timber frame construction and rustic charm. 

The hall features spacious banquet facilities and modern amenities, making it a popular choice for hosting special occasions. 

Over the years, Essenhaus Heritage Hall has become a beloved landmark in the community, attracting visitors from near and far. Its warm hospitality and scenic surroundings make it an ideal setting for creating cherished memories. 

Whether you’re attending a wedding or enjoying a community event, Essenhaus Heritage Hall offers a welcoming atmosphere and a glimpse into the rich cultural heritage of Middlebury, Indiana.


13489 County Road 16, Middlebury, IN 46540, United States

5. Das Dutchman Essenhaus

Savor a taste of authentic Amish cuisine at Das Dutchman Essenhaus, a renowned family-style restaurant serving hearty meals made from scratch. From mouthwatering fried chicken to homemade pies, enjoy a delicious dining experience in a cozy, rustic atmosphere.

Das Dutchman Essenhaus

Das Dutchman Essenhaus was established in 1971 as a family-style restaurant serving authentic Amish cuisine. This iconic eatery has become a staple in the community, known for its hearty meals and cozy atmosphere. 

One interesting fact about Das Dutchman Essenhaus is that it began as a small roadside stand selling homemade pies and baked goods before expanding into a full-service restaurant. 

Over the years, it has grown in popularity, attracting visitors from across the country eager to sample its delicious fare. The restaurant’s menu features traditional Amish dishes and includes fried chicken, mashed potatoes, and homemade pies. 

Das Dutchman Essenhaus has warm hospitality and mouthwatering comfort food and offers a taste of Amish culture and hospitality in the heart of Middlebury, Indiana. The eatery offers a charming ambiance to experience some unique things to do in Middlebury with family.


240 US-20, Middlebury, IN 46540, United States

6. Heritage Ridge Creamery

Take a tour of Heritage Ridge Creamery and learn about the art of cheese making from skilled craftsmen. Sample a variety of handcrafted cheeses, including aged cheddars, creamy goudas, and flavored spreads, and stock up on your favorites to enjoy at home.

Heritage Ridge Creamery

Heritage Ridge Creamery was established in 2015 as a cheese-making facility specializing in handcrafted artisanal cheeses. This modern creamery is dedicated to preserving traditional cheese-making techniques while incorporating innovative flavors and techniques. 

One interesting fact about Heritage Ridge Creamery is that it is located in the heart of Amish Country, surrounded by lush farmland and picturesque landscapes. 

The creamery sources its milk from local Amish dairy farms that ensures the highest quality and freshness in its products. 

Visitors to Heritage Ridge Creamery can take guided tours to learn about the cheese-making process and sample a variety of cheeses, including aged cheddars, creamy goudas, and flavored spreads. 

With its commitment to quality and authenticity, Heritage Ridge Creamery offers a unique culinary experience that celebrates the rich agricultural heritage of Middlebury, Indiana.


11275 W 250 N, Middlebury, IN 46540, United States

7. Krider World’s Fair Garden

You can step back in time at Krider World’s Fair Garden, a historic botanical garden dating back to the 1933 Chicago World’s Fair. Explore themed gardens, scenic pathways, and colorful flower displays, offering a tranquil retreat for nature enthusiasts.

Krider World's Fair Garden

Krider World’s Fair Garden was established in 1933. It is a historic botanical garden located in Middlebury, Indiana. This enchanting garden was initially created for the Chicago World’s Fair, later finding its permanent home in Middlebury. 

One interesting fact about Krider World’s Fair Garden is that it boasts a diverse collection of themed gardens, scenic pathways, and vibrant flower displays, showcasing a wide array of plant species.

Over the years, the garden has become a beloved destination for nature enthusiasts and those seeking a peaceful retreat. Visitors can stroll through the carefully curated landscapes, enjoying the beauty of the various floral arrangements. 

Krider World’s Fair Garden is committed to preserving botanical diversity. It remains a captivating and serene spot for locals and tourists alike and provides a timeless escape into the wonders of nature.


302 Bristol Ave, Middlebury, IN 46540, United States

8. Rise’n Roll Bakery & Deli

Treat yourself to a sweet indulgence at Rise’n Roll Bakery, famous for its mouthwatering donuts and pastries. Choose from an irresistible selection of freshly baked treats, including cinnamon caramel donuts, cherry cheese danishes, and signature cinnamon rolls.

Rise'n Roll Bakery & Deli

Rise’n Roll Bakery & Deli was established in 2001 as a family-owned bakery specializing in handcrafted pastries and baked goods. This beloved establishment quickly gained popularity for its mouthwatering donuts and sweet treats. 

One interesting fact about Rise’n Roll Bakery & Deli is that it is known for its signature cinnamon caramel donuts, which have become a local favorite. The bakery prides itself on using high-quality ingredients and traditional recipes to create delicious baked goods from scratch. 

Over the years, Rise’n Roll Bakery & Deli has expanded its menu to include a variety of pastries, cookies, and deli sandwiches, catering to both sweet and savory cravings. 

With its warm hospitality and irresistible treats, it has become a must-visit destination for locals and visitors to experience fun things to do in Middlebury.


1065 N 1150 W, Middlebury, IN 46540, United States

9. Middlebury Community Historical Museum

Immerse yourself in the town’s history at the Middlebury Community Historical Museum, housed in a restored 1896 Victorian home. Browse exhibits showcasing local artifacts, photographs, and memorabilia, providing insights into Middlebury’s past.

Middlebury Community Historical Museum

The Middlebury Community Historical Museum was established in 1975. This museum showcases a wide range of artifacts, photographs, and memorabilia that tell the story of Middlebury’s past. 

One interesting fact about the Middlebury Community Historical Museum is that it is housed in a restored 1896 Victorian home, adding to its charm and historical significance. 

The museum’s exhibits highlight various aspects of local history, including early settlement, agriculture, industry, and community life. Visitors can explore the museum’s collections and learn about the people and events that shaped Middlebury over the years. 

The Middlebury Community Historical Museum serves as a valuable resource for residents and visitors alike, providing insights into the rich history of Middlebury, Indiana.


301 Bristol Ave, Middlebury, IN 46540, United States

10. Miller’s Cider Mill

Miller’s Cider Mill was established in 2001 as a family-owned cider mill and orchard. This charming establishment quickly became a local favorite for its fresh apple cider and homemade apple products. 

Miller’s Cider Mill

One interesting fact about Miller’s Cider Mill is that it is located on a historic farmstead dating back to the early 1900s, adding to its rustic appeal. 

The mill produces a variety of apple products, including cider, applesauce, and apple butter, using traditional methods and locally sourced apples. 

Visitors can tour the mill and watch the cider-making process in action, from pressing the apples to bottling the fresh cider. With its picturesque setting and delicious apple treats, Miller’s Cider Mill offers a delightful experience for families in Middlebury, Indiana.


55514 County Road 8, Middlebury, IN 46540, United States


Whether you’re seeking cultural experiences, outdoor adventures, or culinary delights, Middlebury, Indiana, offers a diverse range of activities guaranteed to provide fun and entertainment for visitors of all ages. 

Plan your visit today and discover the charm and hospitality of this quaint Midwestern town. Explore some fun things to do in Middlebury, Indiana.