Downtown Lexington

About Downtown Lexington

Downtown Lexington isn't really one neighborhood. It's a cluster of sub-districts, each with its own character. The downtown core includes Triangle Park, Cheapside, Main Street, and the area around the old courthouse. Just north and west you have Gratz Park (one of Lexington's oldest historic districts), the rapidly growing North Limestone (NoLi) area, and the historic Aylesford Place. Just west of the core is the Distillery District, technically its own district but close enough that downtown residents walk or drive to it regularly. For me, "downtown" means going to Fayette Cigar Store on North Mill, picking out a nice cigar, and then strolling over to Triangle Park to smoke it while I people-watch and listen to the water. The Triangle Park waterfall feature is one of the most distinctive downtown landmarks, and there's a real peace to sitting near it on a decent day, even surrounded by city traffic.

What's Nearby

The downtown core itself centers on Main Street and the small commercial strip around Cheapside Park, which sits right next to the old courthouse. Many of the East Main Street restaurants I mention on the Bell Court neighborhood page are right here: Carson's, Jeff Ruby's, V at The Vine, Tony's, Tapster, Lex Live. If you only have one steakhouse dinner downtown, my pick is Tony's. I've had the best steak of my life there, and their bourbon whipped sweet potatoes are so good you'll almost want to eat the plate. Jeff Ruby's is good too, but my favorite is Tony's. Lex Live is a downtown entertainment venue I've been to multiple times. We went to Lex Live and sat at the bar, had a few drinks, then saw a movie on what is supposedly the largest movie screen in Kentucky. They also have bowling, and I think laser tag but I'm not completely sure. The screen is definitely the biggest in Lexington. It's the kind of place where you can spend a whole afternoon, whether you're there with kids, friends, or a date. For drinks and atmosphere, Bigg Blue Martini is one of my go-tos, reviewed in my best-things-to-do guide. The Distillery District sits about a mile west of the downtown core on Manchester Street. It's its own district, not strictly downtown, but close enough that downtown residents access it regularly. The 25-acre site grew up around the historic James E. Pepper Distillery (founded 1879, abandoned 1958, revitalized starting in 2008). Today it's anchored by The Manchester Hotel, Manchester Music Hall, and a cluster of restaurants and bars. I've been to the Distillery District many times. A few specific recommendations: Ethereal Brewing makes great beers. If you love a good IPA, get Wanderland. Goodfellas Pizzeria is one of my go-to pizza spots in the Distillery District. I've written about it in my best things to do in Lexington guide. Crank and Boom Ice Cream is excellent. My favorite is the bourbon and honey. You have to try it. Halligan's Bar and Grill is a Distillery District favorite. I have a whole blog entry about it, go read it. Desperados Cantina at 1224 Manchester Street is a great Mexican restaurant in the Distillery District. Get their deep-fried avocados. I wasn't sure how it would work or taste at first, but it has become a favorite. Gratz Park is one of Lexington's oldest historic districts, a small residential area near the Lexington Public Library with historic homes and tree-lined streets. It's primarily residential and worth a walk if you appreciate historic architecture. North Limestone (NoLi) is just north of Main Street and has become one of Lexington's fastest-changing commercial areas in recent years. Rupp Arena is the heart of downtown's entertainment scene and the home of University of Kentucky men's basketball. I've been to Rupp Arena many times for UK basketball games. The energy is dynamic and something you don't forget. When the team is doing well, the whole place goes crazy. Beyond basketball, Rupp hosts concerts, family shows, and major events throughout the year. The Lexington Opera House (across from Rupp) hosts touring Broadway shows, classical performances, and other cultural events. The Manchester Music Hall in the Distillery District also pulls in larger touring acts.

Annual Events

Downtown is where most of Lexington's biggest annual events happen. All five run on or near Main Street and are walkable for downtown residents. Alltech Lexington St. Patrick's Parade and Festival in mid-March takes over Main Street with a colorful parade and street festival. Mayfest Arts Fair in May is held at Gratz Park with up to 100 artist vendors and live music. Central Bank Thursday Night Live is a weekly summer concert series running from April through October. Fourth of July Parade runs down Main Street from Midland to Mill at noon, with a downtown festival and 10 PM fireworks display. Halloween Festival and Thriller Parade in late October is Lexington's biggest free Halloween event. The Thriller reenactment dance is the headline. USA Today has called it a Top 10 Halloween Destination and Oprah Magazine ranked it among the Top 25 Best Halloween Festivals in the U.S.

Highlights

• Multiple sub-districts (Gratz Park, NoLi, Aylesford Place, downtown core)
• Rupp Arena and Lexington Opera House
• Walking distance to Distillery District
• Triangle Park and Cheapside
• Hub for Lexington's biggest annual events