LEXtoday City Guide Live Banner

Neighborhood Guide: Ashland Park + Chevy Chase

From where to eat + drink to its humble beginnings, we’re sharing all there is to know about the Ashland Park and Chevy Chase neighborhoods.

The facade of Henry Clay's mansion

Ashland, the Henry Clay Estate, is located off Richmond Road on Sycamore Lane. | Photo courtesy of VisitLEX

Arguably some of the most coveted historical neighborhoods in Lexington, Ashland Park + Chevy Chase are synonymous with those old school, small-town vibes. People are often seen walking around the neighborhood or taking a leisurely bike ride to a local shop. Fun fact: Ashland Park was recently named the No. 7 neighborhood with the most luxurious landscape in the US.

Need to know

You’re not the only one with your eyes set on Chevy Chase + Ashland Park. The few homes that hit the market in the area — there were only five in April 2024 — sell in ~35 days. Wondering why? While we can’t say for sure, Chevy Chase is known for its blend of things to do for families + college students alike, walkability, and top-ranked elementary and high schools.

The early days

In the early 1800s, Chevy Chase + Ashland Park were originally one in the same. Both were a part of the 600-acre, all-encompassing estate of Statesman Henry Clay. It wasn’t until the 1920s that Henry Clay Simpson, a direct descendant of Clay, created Chevy Chase. The name — unfortunately not from the well-known comedian and actor — actually comes from a Maryland Golf Course that Simpson once belonged to.

Completed in the 1930s, Ashland Park is listed on the National Register of Historic Places and home to Ashland, the Henry Clay Estate. Today, the neighborhood is home to one Lexington’s oldest businesses, Oram’s Florist.

Catalpa Rd lined with golden gingko trees with the peek of the sun through the trees at sunset.

“Catalpa Rd at Golden Hour” | Photo submitted by Sydney C

Can’t miss

You can’t visit the area without taking a stroll through the picturesque streets of Ashland Park. Take a break from your walk to grab lunch at the Ginkgo Tree Cafe located at the park. If you’re there in the fall when the restaurant is closed, the actual ginkgo trees on Catalpa Road will more than make up for it. Plus, the smell might deter the hunger pangs.

For a more lively atmosphere, venture to the main strip — Euclid Avenue — to sip on a White Russian at Charlie Brown’s or brave the stage for karaoke at the LEX’s oldest dive bar, Chevy Chase Inn. A quick bike ride to Romany Road will take you to other classic neighborhood spots like A.P. Suggins, The Tulip Bistro & Bar, and Wheeler Pharmacy — famous for their malts + milkshakes.

A big white house with a welcoming porch.

Peggy’s has a variety of gifts in all price ranges. | Photo by The LEXtoday


Whether you’re shopping for a gift for yourself or your pup, there’s plenty of local spots nestled in the neighborhood.

  • Worlds Apart + Peggy’s are Lexington staples for all things gifts and home decor.
  • If you’re in the market for a new outfit, pop into Peplum or Monkee’s for the latest styles clothing and accessories.
  • Get off on the right foot for all your fitness needs at John’s Run/Walk Shop. Bonus: This local spot hosts a weekly run club + sponsors numerous races.
  • Happy hour isn’t just for the humans. Pet Wants hosts yappy hour for the fur babies from 4 p.m. until closing time, giving you buy-one-get-one half off chew bar treats.
A shot of Euclid Avenue and Chevy Chase Inn in Lexington Ky

Ain’t no party like a Chevy Chase Street party. | Photo by @nickgerlich

Eat + Drink

There’s no shortage of flavorful local stops from our neighbors in the 40502.

  • Get your breakfast favorites seven days a week at Josie’s, or the sip a specialty brunch cocktail al fresco at the cozy Bella Cafe & Grill.
  • Discover dishes with a Cajun twist from Bourbon n’ Toulouse or get a taste of Greek food at Athenian Grill. Get the baklava — you won’t regret it.
  • For fans of the sudsy stuff, Beer Trappe has you covered with 500+ varieties of bottles, cans, and brews on tap.
  • Sushi lovers will not be disappointed with creative rolls + sake options at Omakase.


If you’ve fueled up and shopped til you’re about to drop, here are a few other area attractions.

  • Satisfy your sweet tooth + enjoy the cozy atmosphere with a pastry and latte from Brevede.
  • Break a sweat at area studios including Creative Yoga, LEX Method, and Pure Barre.
  • Plan ahead for the upcoming Chevy Chase Street Fair on Saturday, June 29, where Euclid Avenue will shut down for live music, vendors, and opportunities to mingle with fellow community members.

Getting around

These two neighborhoods are arguably some of the easiest neighborhoods in LEX to get your scoot, skate, or bike on. They have a close proximity to essential businesses like dry cleaners, a hardware store, and grocery. In fact, Ashland Park is the fifth most walkable neighborhood in our city.

Where to live

It’s time to move quick. This area is so popular, houses sell within weeks. If you’re sold + looking to buy a home in the area, here are some of the current housing options on the market…for now:

  • Stone storybook home, 1003 Tates Creek Rd. | 4 BD, 3 BA | $759,900 | This charming historic home with modern amenities includes a recently updated primary suite with double vanity and claw foot tub.
  • Timeless two-story, 321 Sycamore Rd. | 5 BD, 4.5 BA | $1.19 million | This 1930s classic brick home has been lovingly updated with sparkling wood floors, upscale kitchen with an attached walk-out deck, and a three-car garage.
  • Charming top-floor condo, 1400 Fontaine Rd., Apt. 4 | 2 BD, 1 BA | $319,000 | This apartment has beautifully restored hardwood floors, brand new kitchen appliances, and an in-unit washer and dryer.
Check out our other Guides
We’ve broken down the cost of living in Lexington, KY, comparing it to other states and the US national average.
If wedding bells are in your future, check out these quintessentially Lexington venues.
Ready for your lunch break? Check out these 21 lunches from Downtown to Beaumont.
From the Lexington Legends to the Lexington Sporting Club, we’re sharing all the details of Lexington KY’s sports teams.
Whether you’re a history buff, art aficionado, or sports fan, these 13 museums in Lexington have it all.
Dig into delicious and nutritious vegan and vegetarian fare in every corner of Lexington, KY.
Check out these brunch restaurants, cafes, and diners in Lexington, serving a variety of egg dishes, mimosas, bloody marys, and more.
These 10 hiking trails cater to all skill levels in and around town.
Make the most of the warm weather with this list of the best local summer events and activities.
If you don’t have coffee already in hand, consider this your sign to grab some.
LEXtoday phone
Good news for Lexington.
Get the best local news & events sent to your inbox each morning, for free.