Travel Guide to Lexington, KY: How to Spend a Weekend in Lexington Like a Local

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I moved to Lexington, Kentucky as a newlywed 10 years ago to go to law school, never expecting to stay. Fast-forward to now, where I never want to leave. Lexington is such a great town to visit, and I’m lucky to call it my home. I get a lot of questions about what to do in Lexington, KY when people visit, so I’m putting all of my recommendations together in a post. Here’s how to spend a weekend in Lexington like a local.


If you’re coming to Lexington to visit and need to spend the night, here are three cool hotels that will give you a taste of the city life:

  • 21C Hotel Lexington: This is a boutique hotel located in a historical building in the heart of downtown. The cool thing about this hotel is that it is also a contemporary art museum.
  • Residence Inn Lexington City Center: This hotel is actually right across from 21C, and is a new build that just opened.
  • Origin Lexington Hotel: This hotel is out Nicholasville Road. Located at The Summit at Fritz Farm, it sits in the middle of tons of shops and restaurants.


When I travel to a new city, I always want to know where the locals love to eat. Here are some of my favorite places to eat in Lexington:

Where to Eat Breakfast/Brunch in Lexington, KY

  • Spalding’s Bakery: this is a family-owned bakery that has been around for around 80 years or so. The donuts here are basic but amazing. It’s grab and go, but make sure to have cash on hand as they don’t take cards.
  • Josie’s: Josie’s is such a cute location, but be prepared for a little bit of a wait on the weekends. The whipped cream they put on the pancakes is magical. This is my favorite brunch spot.
  • Doodle’s: And this is Chauncey’s favorite brunch spot. Their motto is “comfort food with a conscience,” and they serve up delicious, locally-sourced meals. Don’t miss out on their beignets.

Where to Eat Lunch + Dinner in Lexington, KY

Lexington’s food scene has exploded in recent years. There are so many amazing places to eat. I’m just going to do a quick run-down of some of my favorites. For a more comprehensive look at what restaurants in Lexington offer, check out my friend Leela’s blog Lex Eats.

  • Malone’s: local steakhouse that’s great for a sit-down meal. Everyone raves about their Lexingtonian salad. Their food is so flavorful and fresh.
  • Joe Bologna’s: if you’re local, then you call it “Joe B’s”. Joe B’s is a casual pizza place that’s in a former synagogue. Make sure to get a breadstick with garlic butter, and no, you won’t want to split it with anyone.
  • Carson’s Food & Drink: great food and vibe. We love to grab lunch or dinner on their patio in the warmer months.
  • Pearl’s: this is a very small pizza place serving wood-fired pizza, shellfish, and salads. This is Chauncey’s favorite pizza place.
  • Ramsey’s Diner: Ramsey’s is the place to go if you’re looking for “home-cookin'”. Very casual and laid-back, they serve regional favorites. And for dessert, make sure to grab a slice of Missy’s Pies.
  • Wallace Station: if it’s a pretty day and you’re looking to take a scenic drive, Wallace Station is must! Sit outside on the back patio for a relaxing meal in the countryside.

Where to Go After Dinner in Lexington, KY


Lexington is a historical town with lots to see and do. I’m sharing some of the “big” things to checkout in town, but for more in-depth recommendations, check out my friend Whitney’s blog, Fabulous in Fayette. Here are some of the things to check out when you come to town:

  • Walk the historical districts downtown. For a starting point, begin at Gratz Park near Transylvania University’s campus. Be sure to read all of the historical markers you spot.
  • Keeneland: If you’re into horseracing, Keeneland’s meet runs every April and every October (checkout their website for details), but you can also visit throughout the rest of the year as well.
  • Kentucky Horse Park: Lexington is definitely horse country. You can tour the horse park, and they host many equine-related events there as well.
  • Rupp Arena: Go catch a University of Kentucky Men’s Basketball game. It’s a super fun experience with crazy energy.
  • Bourbon tours: Lexington is also in bourbon country. You can checkout the Kentucky Bourbon Trail to visit bourbon distilleries in the surrounding area, like Buffalo Trace and Woodford Reserve.
  • Breweries: if breweries are more your thing, check out West Sixth Brewing, Country Boy Brewing, Mirror Twin Brewing, and Etheral Brewing.
  • And if you want a cute photo op, checkout this LEX sign right outside the Historic Courthouse that houses Limestone Hall and Zim’s Cafe. Zim’s is a great food option if you can’t make it out to Wallace Station, as they are both Ouita Michel restaurants.

Hope this helps if you’re thinking about visiting Lexington, Kentucky. It’s truly a great little town, and makes for an awesome weekend getaway. Keep reading for outfit details.

oversized mockneck sweatshirt–$13.49 w/ code OHSALE25 // leggings // Lilly Pulitzer headband (similar, similar) // sunglasses // glitter clutch // glitter tennis shoes // earrings

This outfit is the perfect site-seeing outfit for wintertime! If you’re coming to Lexington in the winter, it’s always a good idea to check the forecast and wear layers, because the weather is all over the place at that time of year. My sweatshirt is the ultimate level of cozy, but SIZE DOWN. I’m wearing my normal size here because they didn’t have the smaller size in this color and I had to have it anyways.

My glitter sneakers are cute, but always won’t kill your feet while you’re walking around downtown. I kept the rest of my accessories simple, including these Kendra Scott earrings Chauncey got me for Christmas.


Nice to meet you!

Hi there! I’m Tif Fannin, the blogger behind Bright on a Budget, based in Lexington, Kentucky. Bright on a Budget is a Southern fashion and lifestyle blog where I share everyday looks, beauty, and travel, along with a behind-the-scenes look at my life as a working mom of two. I have a penchant for bright colors + good deals. Follow along for posts that are relatable to the everyday woman.

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