There are few places left in America that have a unique regional feel. Louisville, founded in 1778, is one of them. It is an amazing city of unique and independent neighborhoods. There is so much to do: walk through Old Louisville to enjoy the collection of old homes, shop in Lulu (the new urban hipster hood just east of downtown), enjoy the independent shops and restaurants (and new local hotel) in the Highlands along Bardstown Road, and experience 4th Street downtown.

The city is very gay friendly and reportedly has not one but two Pride events each year. Foodies will love the unique pan Southern cuisine – lots of fried chicken and bourbon to wash it down. Here is a run down of what to do in each of the many very unique (and tragically hip) neighborhoods:

The Highlands: Weird, Independent, and Proud

This hip and swanky (and LGBTQ friendly) neighborhood is full of unique local shops and restaurants. Bardstown Road is the main thoroughfare.

To do:

Cherokee Park – This Olmstead designed park is a must with miles of hiking and scenery. Nearby is Taylor Park, another Olmstead treasure. Frederick Law Olmstead (of Central Park fame in New York) designed a system of parks and byways in Louisville. Try the coffee at Heine Brothers, the local coffee chain. The fabulous Carmichael’s Books, one of the last great independent book stores left in the country is another Bardstown Road treasure.

New Bellwether Hotel in the Highlight and is located in a recycled police precinct headquarters and also telephone switching station. The is the first and only hotel in the Highlands. You can walk to 3 of the 4 LGBTQ bars and also enjoy the great nearby restaurants. The Bellwether opened in September and is in 2 recycled old buildings: the local police station as well as the old telephone switching station. Enjoy free Netflix streaming in your room and complimentary Heine Brothers coffee. Book your stay at thebellwether.com. You won’t need a car if you stay here since you can walk to all the neighborhood attractions.

Walk to the close together LGBTQ bars including Big Bar (1202 Bardstown Road) which features the best happy hour, Chill Bar (1117 Bardstown) which has karaoke and great music, and the Nowhere Bar (1133 Bardstown Road). They are all steps from each other on Bardstown Road.


Unique shops in this new hipster hangout include include Blofish (gender neutral clothing) and Woman Owned Wallet, as well as the Macaroon Bar for a cookie treat. Enjoy an arepa (a Venezuelan pocket  sandwich) at Senora Arepas. Next to it is LaBodeuita which features Cuban fare. Angel’s Envy Distillery is another must featuring artesian premium whiskey. They also give tours.


Shop at Butchertown Market which features local crafts, antiques, and home furnishings ($1 mimosas). Dance the night away at The Play Dance Bar is a Louisville staple and features three drag shows on Saturday nights plus a nightclub. Tour or eat at Cooper and Kings, a brandy distillery. Yes in addition to bourbon distilleries they have a brandy distillery and rooftop bar and restaurant.

Old Louisville

A historic preservation district with a wide variety of building styles constructed between 1880 and 1905. 1,400 old houses in 45 square blocks make it a treasure of American residential architecture. Book tours here.

Logan Street Market is Louisville’s public urban market and another hipster hangout full of unique shops.


Enjoy a museum in a hotel at Museum 21c Hotel. Very LGBTQ friendly in this unique lodging experience. This arts oriented hotel is tops. I also stayed at the fabulous new Omni which has hints of city history in this luxurious hotel.

Getting there

Just a 5 hour drive from Chicago, I 65 is an option. You can also connect via Midway or O’Hare including on Southwest.  Fares from $59 one way.

Other tips

Lots of local fare including their own ginger ale, Ale8, which packs a punch and is a must.  The Hot Brown sandwich (Mornay  sauce over turkey on Texas Toast) is not for those on a diet. (Details and a recipe at culinary Louisville.com).  Did I mention the Old Fashioned and bourbon selections? I like Marker’s Mark.

You will be amazed at the local fare which makes a trip to Bourbon City a unique gay adventure.

For more information

GotoLouisville.com has all you need to plan your trip.

LouisvillePride.com has the latest on the upcoming prides. LEO Weekly is the independent newspaper ( with all the latest happenings. It stands for the Louisville Eccentric Observer.

Special thanks to GoToLouisville and the Bellwether Hotel for their hospitality and travel tips.


About the Author

Bill Malcolm is the nation’s only LGBTQ+ syndicated value travel columnist. Residing in Indianapolis, he travels with a focus on the local and value orientation.