When the air is crisp and the leaves are changing, there are a few Louisville experiences that always pull us away from the Inn at Woodhaven for a fun day out on the town.

If you happen to be visiting Louisville, Kentucky in the fall months, you are in for a treat. From bold, colorful foliage to fall festivals, haunted spaces, and events around town, there is so much to explore!

We’ve put together a small list of our 11 favorite ways to spend the day when the temperatures start to drop, including hot meals, seasonal treats, unique shopping, and a few events you won’t want to miss. So, toss on your favorite sweater and let’s get ready to explore Louisville together!

1. Family Fun at Churchill Downs

• Location: Churchill Downs, 704 Central Avenue, Louisville, KY 40208
• Drive time from Inn: 17 minutes
• When: Year-round

Our visitors at the Inn at Woodhaven are sometimes surprised when we recommend a trip to Churchill Downs because, well… it just seems like an obvious tourist destination. After all, the Kentucky Derby Museum alone welcomes over 230,000 visitors each year!

Little do they know that the home of the Kentucky Derby is not just a tourist hot spot, we locals enjoy spending time there as well to simply enjoy a cocktail and catch a race. A visit here is always rich in history and steeped in local culture, with a variety of events held each month.

If you’re in town for Halloween with your children, then be sure to grab your tickets for Trick or Treat at the Track on October 26th, 2025. While Old Louisville and its stunning Victorian era homes is a great place for trick or treating, the famous track truly makes it a night to remember! There are plenty of fun things for children under 12, plus a fun day of racing that everyone can enjoy.

Pro Tip: Make some fun side bets with your kids on your favorite horses and maybe you can win some of their Reese’s Peanut Butter cups.

2. Grab a Hot Brown Sandwich from Lou Lou

• Location: Lou Lou Food and Drink, 108 Sears Ave, Louisville, KY 40207
• Drive time from Inn: 5 minutes
• When: Year-round but best enjoyed in colder weather

Have you ever had a Hot Brown sandwich? If you haven’t, you are missing out on a true Louisville classic! A Hot Brown is an open-faced hot turkey sandwich with smoked bacon and Mornay sauce. It was originally created by the Brown Hotel back in 1923 to feed the late-night dance crowd. Think of it like the Denny’s “Moons Over My Hammy” of the roaring 20’s. If you want to become a local sandwich history buff, you can learn more HERE.

A Hot Brown at Lou Lou Food and Drink (located just down the road from our bed and breakfast) also happens to be one of our favorite meals to enjoy on a cool October day. If sandwiches aren’t your thing, they have an extensive menu with an eclectic mix of Southern, Cajun, and Italian options, including gluten-free pasta.

Pro tip: If you still have room for dessert (and you should definitely save room for dessert), top off the fall evening by enjoying their pretzel brownie with toasted marshmallow and caramel sauce. Healthy? No. Heavenly? Sure is.

3. Taste Pumpkin Ice-Cream

• Location: Plehn’s Bakery, 3940 Shelbyville Rd, Louisville, KY 40207
• Drive time from Inn: 5 minutes
• When: Fall

When pumpkin patches, pumpkin flavored lattes, and Jack ‘o Lanterns start popping up, why not embrace the chill with a delicious scoop of ice cream?

Plehn’s Bakery (pronounced “Plains”) is another historic spot that was opened in 1922 and four generations later, it is still operated by the family today. But during the fall, we like to grab their homemade pumpkin ice cream which is only available seasonally.

Okay, so we’re sneaking ANOTHER food stop into this list. Is it excessive? Maybe, but when we know of a good thing, we need to share it.

4. Attend the Gaslight festival

• Location: Jeffersontown
• Drive time from Inn: 17 minutes
• When: September 4th to 14th, 2025

For a few glorious days in September, the Louisville suburb of Jeffersontown is home to the magnificent Gaslight Festival.

With a parade, car show and even a pipe smoking competition, there are so many events that it’s almost impossible to list them all. No matter if you decide to come on your own or bring your entire family, there’s something for everybody.

Oh, and did we mention that the Inn at Woodhaven is only a 17-minute drive away from the action??

Get more festivals in our guide: Louisville Fall Festivals 2025

5. Visit the St James Court Art Show

• Location: St. James-Belgravia Historic District, Old Louisville
• Drive time from Inn: 18 minutes
• When: October 3-5, 2025

This amazing annual art show is an example of why Louisville is such a great destination for art lovers! In the first week of October, 600 artists from all over the country display their work against the beautiful backdrop of Old Louisville.

Whether you’re interested in painting, sculpture or just the delicious food, the art show has plenty to offer to visitors.

6. Celebrate Bourbon Heritage Month

• Location: Kentucky Exposition Center 937 Phillips Lane, Louisville, KY 40209
• Drive time from Inn: 13 minutes
• When: September 11th to 14th

On Main Street in downtown Louisville, you can find the collection of distilleries and bars collectively known as Whiskey Row. While this area near the Ohio river is worth visiting year-round, it is a must in Bourbon Heritage Month!

On September 11-14, Louisville is home to the amazing Bourbon & Beyond Festival. Visitors can enjoy amazing live music, taste great food and of course enjoy a drink or two.

Pro tip: If you prefer to pair your bourbon with food rather than live music, then consider the amazing Beyond the Barrel walking tour! The only one of its kind, this walking tour takes a deep dive into the barrel as you learn all about the rich history and traditions surrounding Kentucky’s favorite spirit!

7. Peep some Leaves at Cave Hill Cemetery

• Location: Cave Hill Cemetery, 701 Baxter Avenue, Louisville, KY 40204
• Drive time from Inn: 14 minutes
• When: Fall 🍂

Gorgeous fall foliage is everywhere around Kentucky, however one of our favorite spots for a wide array of leaf peeping with a decidedly spooky twist is Autumnal Air Tree Tours at Cave Hill Cemetery.

With excursions on October 23rd and November 13th, the Cemetery’s horticulturist and arborist provide an informative tour as you ride through the historic grave sites in an open wagon. Grab a thermos of cider, coffee, or any other hot non-alcoholic beverage to keep you cozy on a journey that may give you the chills in more ways than one.

Pro tip: These ticketed events fill up FAST so if you’re reading this now it may already be too late. Go ahead and book now for next year.

8. Boo at the Louisville Zoo

• Location: Louisville Zoo
• Drive time from Inn: 13 minutes
• When: Select nights in October 2025

While many people visit zoos in summer, Louisville is one of the few zoos worth visiting in the colder months. Sure, October doesn’t sound like the best time to visit a zoo but we urge you to think again!

Every year in October Louisville Zoo hosts Boo At The Zoo, a month filled with Sleepy Hollow-themed fun. Although you might run into the Headless Horseman himself, the festivities are designed to be ‘merry, not scary’ and are suitable for kids 11 and under.

With special nights devoted to trick or treating as well as sensory-friendly and allergy-friendly nights, we believe that the Louisville Zoo is one of the best places in the city for some good old family fun.

9. Shop for Souvenirs and Selfies

• Location: Red Tree NuLu, 701 East Market Street, Louisville, KY 40202
• Drive time from Inn: 15 minutes
• When: Autumn to jumpstart your holiday shopping

Oooh, the courtyard! Take one look at their Instagram photos and you’ll see why Red Tree NuLu is one of our favorite local shops. While area residents love Red Tree for their unique handcrafted furniture, visitors will also appreciate some non-traditional souvenirs from featured local artists and makers.

Do you have to go here in the fall? No, you can go at any time. But we had to include them on this list so that you wouldn’t miss out on one of our favorite spots to browse and buy.

Pro tip: If the art-lover in you needs even more to do, pencil in Louisville’s Via Colori Street Painting Festival in October at 129 W River Road. It features hundreds of artists and community organizations for one awe-inspiring weekend. Another local favorite is Colorfest in Bernheim Forest (in neighboring Clermont).

You may also like: Louisville Ideas for Art Lovers

10. Go for a Stroll in Cherokee Park

• Location: Cherokee Park, 745 Cochran Hill Road, Louisville, KY 40206
• Drive time from Inn: 10 minutes
• When: Leaf peeping season

In fall, Cherokee Park is one of the best free local spots to catch nature at its finest. Cherokee boasts over 380 acres of rolling hills, tree groves, and woodlands, making it a leaf-lover’s paradise. Bring your bike or lace up your walking shoes for a 2.4-mile scenic loop around the park. If you’re in town in October, swing by for their annual Hayride in the Park and enjoy live music, guided hayrides, and family-friendly activities.

Pro tip: Pack a lunch or grab your Hot Brown sandwich to go. This park has plenty of picnic tables and shelters to enjoy an afternoon lunch outdoors.

You may also like: Best Time To See Louisville Foliage

11. Look for Ghosts

• Location: Various cemeteries, theaters, ships, and taverns
• When: October (tis the season, right?)

Kentucky’s state motto is “Unbridled Spirits,” and it’s not just referring to the bourbon! Louisville has many world-famous haunted destinations that beckon the deranged (or curious) visitor. See a preview of what awaits in the below video of the Waverly Hills Sanatorium — leaving the lights on is recommended. Get a full itinerary in our haunted sites in Louisville guide.

The Perfect Fall Weekend Getaway

If you can’t make it to this year’s fall events, consider booking ahead for some fall fun. We’ll be happy to reserve a room for you at the Inn at Woodhaven and offer even more insider tips on how to make the most of your time in this charming town. And if we’ve left any of your local fall favorites off our list, be sure to let us know so that we can include them in the future.