Disclosure: This post is sponsored by Visit Dubois County. As always, all opinions and recommendations are my own.
This cozy fall road trip is just 2.5 hours south of Indianapolis, and if you love slow mornings, homemade cookies, historic churches, and conversations with strangers, you need to save this Dubois County itinerary! My husband and I just spent a lovely fall weekend in Dubois County, Indiana. We stayed in Jasper, Indiana and made an evening trip over to Huntingburg while we were there.
You know how some small towns can make you feel like an outsider? You ask for directions, and they’ll look at you like you just insulted their grandmother? This is NOT the case in Jasper and Huntingburg, Indiana. What you’re going to notice throughout this entire story itinerary is the kindness we were shown by each and every person we encountered in Dubois County.
Every shopkeeper, server, and passerby immediately knew we weren’t from around there, and they welcomed us with open arms, restaurant recommendations, and local stories. It’s a place where everyone knows everyone, yet they are very excited to see new people coming to visit and to talk to them about their town’s history.
If you’re looking for cozy fall getaways in driving distance from Indianapolis, keep reading! We fell in love with Dubois County, and it should definitely be on your list for must-visit destinations in Indiana!
WHERE TO STAY
Winfield West Bed & Breakfast 📍325 West 6th Street, Jasper, Indiana
Winfield West Bed and Breakfast is run by local angels, Regina and Fred. The historic home was built in the 1880s with 4 bedrooms available to guests. Gourmet breakfast is served each morning, made with care by Regina and Fred. Eggs your way, baked pears, fluffy waffles, homemade granola, hot coffee, I mean… can you get any cozier than that?
More Highlights:
- Homemade cookies at bedtime
- Gorgeous front porch and back patio oasis
- Historic architecture and decor
- Coffee bar and refreshments in the upstairs kitchen
- Perfect location near Jasper’s town square
- The best breakfast you’ll ever have
Looking back, Winfield West was the perfect backdrop to our fall weekend in Dubois County. Being greeted by Regina was the first glimpse we received into what our weekend had in store for us, and there couldn’t have been a better way to set the scene.
Another bonus is that it’s located within walking distance of downtown Jasper which we took full advantage of. One thing about me is I love a walkable city, and I always make sure to get lodging close enough to never have to touch my car or order an Uber.
WHERE TO EAT
Butcher and Barrel 📍 416 E 4th St, Huntingburg, Indiana
This fabulous restaurant is inside an old bank. You can actually make reservations to eat inside the bank’s vault! This is definitely one of the most unique places to eat in Huntingburg, and the food, drinks, and service make it even better.
Pink Duck Creamery 📍 402 E 4th St, Huntingburg, Indiana
For me, a fall road trip means all things pumpkin, and Pink Duck Creamery had a brown butter pumpkin ice cream that will live rent free in my head for years to come. We didn’t try these, but they did also have boozy ice cream which we heard great things about!
Wood Capital Pizza 📍 603 Main St, Jasper, Indiana
Am I back in Italy? This wood-fired Margherita pizza was exactly what I needed after a long day of shopping and climbing ladders (stay tuned 👀) in Jasper, Indiana.
Snaps 📍 1115 Main St, Jasper, Indiana
You can tell that Snaps is beloved in Jasper. Every Jasper local we talked to asked us where we were planning on going for dinner. When we said “Snaps” they were very excited for us! It’s the place every shopkeeper, server, and tour guide was planning on telling us to go anyway. And I can attest that I totally understood the hype. Everything we got was delicious and the service was wonderful. Don’t leave without a slice of their homemade cheesecake!
WHERE TO DRINK
Yard Goat Artisan Ales 📍 417 E 4th St, Huntingburg, Indiana
A small brewery right in the heart of Huntingburg, Indiana’s Historic 4th Street making beers and seltzers! P.S. They might’ve dethroned Quaff On as my favorite strawberry blonde.🫣
The Next Chapter 📍 519 Main St, Jasper, Indiana
The cutest coffee shop / book store ever! I got their white pumpkin latte and a souvenir glass because I loved it so much.🤭 It’s right in the heart of Jasper’s square making it the perfect spot for a pick-me-up while you’re shopping around.
The Social Pour 📍 225 River Centre Lndg Apt F, Jasper, Indiana
When you’re planning your road trip to Dubois County do not miss The Social Pour! This is a new wine bar in Jasper that has wine by the glass (or you can get a flight like we did!), games, a walk-up window, cozy seating, moody lighting, and you can bring in your own food! We really enjoyed our time at The Social Pour!
WHERE TO SHOP
Historic 4th Street 📍 Huntingburg, Indiana
The sweetest downtown area with boutiques, restaurants, local events, and more! I felt like I was walking around in a storybook when exploring Huntingburg’s historic 4th street! Here are just a few of the shops we stopped in:
- Downtown Emporium
- Ella & Ivy Homes (I wanted to take home everything in this store)
- Family Roots Nursery
- Gelhausen’s Flowers & Gifts
- Firefly Boutique
- Gypsy Girls
- Rooted Soul Apothecary & Botanicals (we made a fall candle here!)
Downtown Jasper
Jasper, Indiana is home to some adorable boutiques and shops all within walking distance of Winfield West Bed & Breakfast. Here are just a few of the shops we stopped in:
- American Mercantile
- Chocolate Bliss & Kitchen Essentials
- Finishing Touches
- Jasper Flowers & Gifts
- Just Whimsy
- This Olde House (on the site of Jasper’s very first house!)
WHERE TO EXPLORE
The Art Loop in Jasper is a walking route with art installations all over town. It connects the Patoka Riverfront to downtown Jasper with murals, crosswalk art, and other unique pieces. My husband and I got this map and tried to find them all before we left!
The Jasper riverwalk is a 2.1-mile trail along the Patoka River. Don’t miss the one-room schoolhouse and Veteran’s Garden along the route! A relaxing walk in Jasper, Indiana, and when the trees change colors in the fall, I bet it is even more beautiful!
Jasper City Mill 📍 164 Third Ave, Jasper, Indiana
This mill was recently constructed on the Patoka River. We ended our riverwalk adventure here where you can take a tour of the mill, grab some local goodies, and enjoy the sights and sounds of the mill on the river.
THINGS TO DO IN JASPER, INDIANA
A show at The Astra
The Astra 📍517 Main St, Jasper, Indiana
This gorgeous theatre first opened in 1936! We got to see a Bob Seger tribute band at The Astra while we were in town, but the theatre has all kinds of shows, concerts, and movies. Definitely check the schedule when planning your visit!
Climbing to the top of this historic church
St. Joseph Church📍 1029 Kundeck St, Jasper, Indiana
St. Joseph Catholic Church was built in the 1800s and is on the National Register of Historic Places. We were lucky enough to meet Jill and Bob (more local angels) who gave us the entire history of St. Joseph from its conception to the most recent remodel. Their faith and love for their church is beyond inspiring, and we learned so much about not only the church but Jasper as a whole. Jill and Bob took us all the way to the top of the bell tower via a lot of stairs and ladders! From the top of the bell tower, looking out at Jasper in all directions, we learned about the city’s German roots, its immense love for baseball, and so much more. We also got to sign our names at the top, so a piece of us will always stay in Dubois County. Truly an unforgettable experience that I recommend to everyone wanting to visit Jasper, Indiana. If you want to book this tour, you can call the church at (812) 482-1805.
There you have it! The most perfect cozy fall getaway to Dubois County, Indiana. If you’re looking for road trip destinations in Indiana to visit this fall, I hope you’ll consider this itinerary for your next couples getaway or family road trip!
Disclosure: This post is sponsored by Visit Dubois County, which hosted my trip and provided accommodations and experiences. I may have received compensation for this partnership. As always, all opinions and recommendations are my own.
