Day-by-day eating plans for Lexington. weekend classics, family routes, vegan plans, on-a-budget editions.

Day-by-day plans

Lexington bourbon weekend, done properly ★ 4.6

First-time visitor, two days2 days

Two days built around bourbon country's home city: a distillery-and-brewery crawl through the Distillery District, beer cheese and burgoo where locals eat them, and nightcaps from Kentucky's largest bourbon wall.

  1. Day 1: Day 1: downtown, Town Branch and Jefferson Street

    Morning
    Doodles at 08:00 for dirty shrimp and grits in the converted petrol station on North Limestone. Walk it off around the courthouse square afterwards.
    Afternoon
    Book the Lexington Brewing & Distilling tour on Cross Street, where Kentucky Bourbon Barrel Ale ages beside the Town Branch stills, then cross to Crank & Boom on Manchester Street for a bourbon and honey scoop.
    Evening
    Dinner at Distilled on Jefferson from 17:00, farm-driven Southern cooking with a deep bourbon list. Finish at The Bluegrass Tavern on Cheapside and let the bartender build a flight.

  2. Day 2: Day 2: donuts, the Distillery District and smoked Kentucky meats

    Morning
    Spalding's Bakery by 09:00 for hand-rolled glazed donuts; the trays empty before noon. Take them to Tandy Park if the Saturday farmers' market is running.
    Afternoon
    Spend the afternoon on the James E. Pepper campus: a farmhouse pint at Ethereal Brewing, then a cask tasting at Dark Arts Whiskey House a few doors along Manchester Street.
    Evening
    County Club smokes Kentucky beef, hog and goat on Jefferson Street from 17:00, Wednesday to Saturday. End upstairs at the Wiseguy Lounge above Goodfellas with a bourbon old fashioned.

Old Lexington: counters, classics and the 1933 barstool ★ 4.4

Returning visitor chasing institutions, two days2 days

Two days of the Lexington that predates the boom: a drugstore lunch counter, a manor-house Southern dinner, burgoo, chess pie and a nightcap at the city's oldest bar.

  1. Day 1: Day 1: Chevy Chase mornings and a downtown dinner

    Morning
    Josie's on Chevy Chase Place from 08:00 for the Chevy Chase Special; expect a weekend queue and take it as part of the ritual.
    Afternoon
    Lunch at Wheeler Pharmacy's counter on Romany Road: a double-stacked Buddy Burger and a malted milkshake between the greeting cards and prescriptions.
    Evening
    Dinner at Dudley's on Short in the old bank block, then a quiet cocktail around the corner at Ona on Church Street.

  2. Day 2: Day 2: burgoo, pie and the oldest bar in town

    Morning
    Winchell's on Southland Drive from 08:00 for a country breakfast; order beer cheese to take away for later if you are travelling on.
    Afternoon
    A bowl of farm-sourced burgoo at Stella's Kentucky Deli on Jefferson Street, then drive to Missy's Pie Shop on East High for a chess pie slice.
    Evening
    The Merrick Inn's manor-house Southern dinner from 16:00, then a last bottle at the Chevy Chase Inn, pouring since 1933.

Lexington on a budget: donuts, tortillas and a taproom ★ 4.2

On a budget, one day1 day

One cheap, excellent day: Greyline Station donuts, the west side's best tortillas, and a fish sandwich inside a brewery, all for well under $40 a head.

  1. Day 1: Day 1: NoLi to Alexandria Drive and back to the Bread Box

    Morning
    North Lime Coffee & Donuts at Greyline Station from 07:00; the strange weekly specials sell out first, and everything closes at 13:00.
    Afternoon
    Cross town to Tortilleria y Taqueria Ramirez on Alexandria Drive for burritos on fresh-pressed tortillas; buy a warm stack to take home.
    Evening
    Back north to the Bread Box building: a West Sixth IPA in the taproom and a fried fish sandwich from Smithtown Seafood through the wall.
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