Louisville Highlands and Cherokee Triangle Food Tour

Discover Louisville’s Victorian Charm — With Local Food, Drinks & No Crowds!
Escape the crowds in Old Louisville and experience a side of the city most visitors miss. Just five minutes from downtown and NuLu, the Highlands is a local’s favorite, home to Louisville’s iconic Victorian architecture and “restaurant row”. Brimming with with tree-lined avenues, opulent Victorian mansions, and quirky charm, this hidden gem is over 50 years older than Old Louisville — and far more delicious!

You’ll stroll tree-lined streets lined with colorful murals and grand historic homes, hear fascinating stories of immigrants, icons, and innovators, and enjoy generous tastings of signature Louisville flavors at beloved local eateries you’d never find on your own.

Unlike Old Louisville’s large group walking tours (no food, no drinks, no fun), this small-group experience includes everything you came to Louisville for: bites, bourbon, history, charm, and no hassle!

Meeting Point

O'Shea's

956 Baxter Ave, Louisville, KY 40204, USA

Meet your guide on the sidewalk in front of the Irish pub at 956 Baxter Avenue. We recommend parking on a side street such as Morton or Highland, and NOT on busy Baxter Ave. (Note: There are two pubs with the same name in Louisville - ensure you are going to the one on Baxter, not Main!)

What's included:

• Admire Victorian-era architecture in a neighborhood 50 years older than "Old Louisville"
• Led by an expert local guide
• 4 Delicious dishes representing Louisville's culinary heritage on Restaurant Row
• Taste a Hot Brown-inspired dish at Muhammed Ali's former boxing gym
• Bourbon tasting at the city's oldest bar, plus craft beer & cocktails
• Dessert and cocktail at a farm-to-table restaurant to end your tour
• The unfiltered history (and glamour) of Louisville's most historic neighborhoods

Not included:

• Transportation

What to expect:

Duration: 3 hours

Louisville

Louisville, Kentucky

Stroll the lush, tree-lined avenues of the Original Highlands and Cherokee Triangle as you see some of the oldest homes in Louisville. This neighborhood predates "Old Louisville" by over 50 years!

2 hours

Cave Hill Cemetery

701 Baxter Ave, , Louisville, 40204-1775, Kentucky

We will pass by the entrance to beautiful Cave Hill Cemetary, the final resting place of Muhammed Ali, Colonel Sanders, and other notable Louisvillians

Pass by without stopping

Cherokee Triangle

Cherokee Triangle, Louisville, KY 40204, USA

This beautiful historic neighborhood is brimming with Victorian mansions, charm, and tree-lined streets.

Pass by without stopping

Original Highlands

Original Highlands, Louisville, KY 40204, USA

Welcome to Restaurant Row! We will stop at 5 locally owned establishments for food, drinks, and stories. Bourbon tasting at the city's oldest bar; a Hot Brown-inspired treat at a gym where Muhammed Ali once trained; a farm-to-table treat topped with Kentucky's favorite southern sweet sauce, and more.

1 hour