End-of-Summer Downtown Date Ideas

By: Claire O’Neill/Harrison Stiles

We’re all trying to soak up as much outdoor time as we can before fall hits. Here are some great ideas for date nights while it’s still warm outside!

  1. The Square

The Square is the perfect place to bring a date. Within only a few blocks radius there’s coffee, restaurants, shopping, and even a park. For lunch you could check out Vinaigrette, a relatively new restaurant known for their gourmet salads and soups. Pies and Pints offers another casual option, with delicious pizza and some cold beer. If you’re looking for something a bit more elegant, look no further than Tony’s. A modern-rustic steakhouse, they offer a regal atmosphere that will make your evening one to remember. Be sure to make some reservations and check out the dress code before you go! After your meal, take your date on a walk through Triangle Park and look at the beautiful fountains while you sip your cold brew coffee from Nate’s Coffee, located right around the corner at Fifth Third Bank Pavilion in Cheapside Park.


  1. The Distillery District

The Distillery District is the ideal date night venue. Goodfellas Pizza has a lively atmosphere that’s perfect for a first date. Their patio is great for a Lexington summer night and they have over 200 varieties of bourbons and drinks in true Kentucky fashion. After a slice, stop in at The Burl for live music or to sit by their outdoor fireplace if you’re looking for a more intimate discussion away from the noise.

  1. Dudley’s and Sky Bar

Start your night at Dudley’s on Short in the heart of downtown for an excellent meal before making your way over to Sky Bar. The two are located only a block apart, making for an easy walk on a nice summer night. On the way you may pass Central Bank Thursday Night Live with live music accompanied by local food and drink vendors. Once you reach Sky Bar, enjoy high spirits and tasteful piano.


  1. Pepper Campus – Battle Axes & Ice Cream

If you’re worried about being nervous on your date, Battle Axes would be the perfect ice breaker. Located in the historic Pepper Campus, Battle Axes is a great place for thrill seekers and beer drinkers alike with over 70 canned ciders and beers. They are paired with an ideal location surrounded by restaurants such as the Elkhorn Tavern, known for its laidback atmosphere, live music and cozy fire pits. Close by is Crank & Boom, the prime location for an ice cream break to beat the heat. I mean one scoop, two spoons? It doesn’t get much more romantic than that.

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