The Perfect Fall Road Trip in Indiana!

Road trip anyone? Fall is the perfect time to take a road trip in Indiana. The leaves are changing, the weather is cooling down, and some of the best festivals and attractions come out in the fall! The best route to take with the most stunning views and fun things to do is Route 20 or Highway 20, which goes through northern Indiana. This route will take visitors through LaGrange County, home of the infamous Shipshewana, a popular destination for Hoosiers and tourists alike. Along the way, there will be plenty of interesting, cozy towns, fun attractions, and delicious restaurants to discover. Get planning!   

1. Songbird Ridge Bed and Breakfast, Shipshewana, IN

The first stop on any road trip should be finding a place to stay, and depending on one’s preference for lodging, there are a variety of B&BS, hotels/motels, campgrounds and RV parks, as well as cabins to be found along Highway 20. If you prefer a bed and breakfast, the Songbird Ridge Bed and Breakfast is the place to stay in Shipshewana! The B&B is in the heart of Amish country and is surrounded by many Amish farms. Picture rolling green hillsides, listen to the sounds of quail birds and ducks as they pass… It’s a true country retreat, made even better by hosts Gene and Gwen, who are absolute gems and make you feel welcome! Though you may enter as guests, you’ll definitely leave as friends. 

2. Kitchen Cupboard, Shipshewana, IN

After a wonderful night’s stay at Songbird Ridge Bed and Breakfast, wake up feeling refreshed and ready to start your day with a healthy breakfast and a good cup of coffee. For the best coffee, head to the Kitchen Cupboard and enjoy the taste of locally-roasted coffee beans. For the best breakfast, try Four Seasons Diner and experience the best omelet and old fashion pancakes you’ve ever tasted!

3. Black Pine Animal Sanctuary, Albion, IN

The best part about Highway 20 is that even though you might be staying in one place, there is always something to do within a 10-15-minute drive. One of the most popular attractions and scenic areas to visit is the Black Pine Animal Sanctuary in Albion, Indiana. Just a short drive from Shipshewana, this non-profit animal sanctuary is a refuge for displaced or captive raised exotic animals to live out the rest of their lives in peace and as in much of a natural environment as possible. There are a variety of tours available, from group tours to private tours, to tadpole tours for the little ones. It’s a great place for the whole family. 

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4. Shipshewana Flea Market, Shipshewana, IN

When taking a road trip, it’s always great to bring back some souvenirs and whether you are visiting Shipshewana, Middlebury, or any of the other destinations along Highway 20, you are bound to walk away with some amazing finds! The next best scenic destination is the Shipshewana Flea Market. With over 800 booths, it is certainly a sight to behold and what everyone comes to see. The market is open rain or shine, but be sure to dress accordingly for the weather as it is an open-air market. Another thing visitors should take note is to most vendors accept credit cards, but it is always a good idea to have plenty of cash on hand!

Spending the morning digging for gold 🤗 #fleamarketfinds

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5. Iannarelli’s Italian Restaurant, Howe, IN

After a day of taking in the sights and shopping, it’s time for lunch. Because visitors find themselves in Amish country, there is no shortage of hot, delicious lunches to be found here! Iannarelli’s Italian Restaurant is the place to go for lunch. Located in Howe, Indiana, Iannarelli’s has the best pizza and Italian food. The food is homemade, hot, fresh and out of the oven. Their lasagna tastes just like Grandma made it, and their pizzas are thin, crispy and melt in your mouth!

My salad is AMAZING, your pizza and bread sticks look horrible @tomndi. #damnit #fatkidproblems

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6. Pumpkin Vine Trail

If you are planning a weekend trip, it’s best to save these next destinations for your second or third day. Start your morning off with an energizing hike through the Pumpkin Vine Trail. The trail itself was once a railroad line that connected the towns of Goshen, Middlebury, and Shipshewana. Now, visitors from all over come to hike, walk, bike and run this trail. The trail is smooth yet somewhat challenging and comes with beautiful views: rural areas, farm fields, country roads, tunnels through forests, acres and acres of corn fields… The views are diverse and provide a scenic view as you hike. 

7. Kercher’s Sunrise Orchards, Goshen, IN

Fall in Indiana means it is apple picking season and the orchards are in full bloom! Visit Kercher’s Sunrise Orchards in nearby Goshen, Indiana. Family owned and operated since 1922, the orchard is a favorite of Hoosiers and visitors alike. From now through November, visitors can come and pick their own delicious apples. Enjoy a wide variety of Honey Crisp apples, Cortland apples, Red and Golden Delicious apples, as well as Fuji and Granny Smith. 

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8. Winchester Mansion, Elkhart, IN

With Halloween just a little over a month away, now is a good time to start visiting the haunted houses and attractions! Because Indiana is rich with history, you’ll be hard pressed to find an attraction that isn’t haunted, especially in northern Indiana. Take a tour of the legendary Winchester Mansion in Elkhart, Indiana, where visitors are said to have seen the ghost of a former resident, Miss Nellie Knickerbocker and experienced lights in the attic turning off by themselves, items falling off the shelves, and strange sounds in the night. Rumor has it that Miss Nellie was a bit quirky. She’s said to have liked her husband’s casket so much, she bought one for herself and kept it in the foyer. Quirky, huh?

9. 41 Degrees North Restaurant and Bar, Middlebury, IN

At the end of the day, after you’ve toured the apple orchard, had an energizing hike, and finished up the evening with a tour of a haunted house, it’s always nice to unwind with friends, family, and a good drink. The best place to do this is at 41 Degrees North Restaurant and Bar in Middlebury, Indiana. The restaurant features a full-service bar, two large TVs, bar top dining, and it’s also family friendly. They’ve only been in business for a few years, but have already made a name for themselves. Try one of their delicious signature cocktails, wine offerings, or a draft beer or bottle!

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