Where to Eat on Park Avenue South, Block by Block

Park Avenue South runs a straight eight blocks between Union Square and Gramercy Park, and it carries a tight cluster of Italian kitchens along the way, some right on the avenue and others a few steps off it on the cross streets. If you’re standing at the 14th Street subway hub trying to decide which way to walk, here’s a block-by-block rundown of what’s actually there.

Short answer: working north from Union Square, the strongest Italian options directly on or just off Park Avenue South are Tarallucci e Vino and Paul & Jimmy’s near 18th Street, Union Square Cafe and Isabelle’s Osteria around 19th and 20th, Rezdôra near 20th, and Giorgio’s of Gramercy at 21st, right by the park gates.

At a Glance

• Nearest subway: 4/5/6 to 14th St–Union Square or 23rd St; N/Q/R/W to 14th St–Union Square
• Corridor length: about eight blocks, roughly a 12–15 minute walk end to end
• Note on naming: the avenue is called Union Square East from 14th to 17th Street, then becomes Park Avenue South from 17th Street north
• Best for a fast solo dinner: Tarallucci e Vino or Paul & Jimmy’s
• Best for a special-occasion table: Rezdôra
• Best for a Park Avenue South address with handmade pasta: Isabelle’s Osteria

Why Park Avenue South Works as a Walking Spine

Most Gramercy dining guides cover the wider triangle between Union Square, Flatiron, and Gramercy Park. This one sticks to a single street. Park Avenue South (and its downtown extension, Union Square East) is a straight north-south line, so you don’t need a map. Just walk it and check cross streets as you go.

Technically, the stretch from 14th to 17th Street is signed Union Square East, and the name changes to Park Avenue South once you cross 17th. For a walking guide it’s one continuous line, so we’re treating the whole run from Union Square to Gramercy Park as a single corridor.

Starting Point: Union Square, 14th Street

Begin at the 14th Street–Union Square station, served by the 4, 5, 6, N, Q, R, and W lines (the L also stops here, though it’s not part of the core lines for this walk). This is the widest transit hub on the route and the obvious starting block whether you’re coming from downtown or uptown.

From here, Park Avenue South (as Union Square East) runs north past the top of the square toward 17th Street, where the block starts to narrow and the restaurant density picks up.

17th to 18th Street: Tarallucci e Vino and Paul & Jimmy’s

Tarallucci e Vino sits at 15 East 18th Street, between Broadway and Park Avenue South, a short detour off the avenue itself. According to the restaurant’s own site, this location is open Monday through Thursday from 8 a.m. to 10:30 p.m., Friday until 11 p.m., Saturday from 9 a.m. to 11 p.m., and Sunday from 11 a.m. to 10:30 p.m., with happy hour offered at the bar and outdoor tables in the afternoon. It works if you want something Italian earlier in the day: coffee and pastry in the morning, a panino at lunch, pasta at dinner, none of it requiring a reservation.

A block east, Paul & Jimmy’s has held its spot at 123 East 18th Street, between Irving Place and Park Avenue South, since 1950. Per the restaurant’s website, current hours run Monday from noon to 9 p.m., Tuesday through Saturday from noon to 10 p.m., and Sunday from noon to 9 p.m., with a weekend brunch menu offered Saturday and Sunday from noon to 3:30 p.m. The menu leans Italian-American classics, the kind of place where a regular has a usual order.

19th Street: Union Square Cafe and Isabelle’s Osteria

Union Square Cafe sits at 101 East 19th Street, between Park Avenue South and Irving Place. Its own site describes the kitchen as New American, not Italian, though the seasonal cooking draws openly on Italian technique and ingredients. It’s worth knowing about if you want that sensibility without a strictly Italian menu.

For dinner that’s Italian in both name and menu, Isabelle’s Osteria is a short walk further, at 245 Park Avenue South between 19th and 20th Street. It sits directly on the avenue rather than around the corner from it, which makes it a fitting anchor for this particular walk, and it’s built around handmade pastas and seasonal dishes. It suits a sit-down dinner more than a quick bite: a date, a small group after work, a table before heading over to Gramercy Park. According to the restaurant’s own hours page, it’s open daily starting at 11:30 a.m. on weekdays and 10 a.m. on weekends, running into the evening. Given how directly it sits on the avenue this guide is built around, it’s worth a look. Check its current menu on its own site before booking, since seasonal dishes rotate.

For groups that need something more private than a shared dining room, it’s worth comparing how private dining rooms in this part of Gramercy stack up before you call to book.

20th Street: Rezdôra

One block north and just off the avenue, at 27 East 20th Street between Broadway and Park Avenue South, Rezdôra is the corridor’s reservation-first kitchen. It’s an Emilia-Romagna-focused Italian restaurant, and per its own site, hours run lunch and dinner Tuesday through Sunday, with dinner-only service on Monday. Book ahead. This is the stop built for a night that’s the whole plan, not a quick detour on the way somewhere else.

21st Street: Giorgio’s of Gramercy, at the Park Gates

The corridor ends at 21st Street, right at the edge of Gramercy Park, where Giorgio’s of Gramercy has sat at 27 East 21st Street for decades under that name. Per the restaurant’s own site, the kitchen serves an Italian-American menu of pastas, salads, and mains in a room that reads more neighborhood trattoria than special-occasion destination. It closes out this stretch of Italian dining near Union Square eight blocks later, almost at the park’s front gate. Check the restaurant’s current hours before visiting, since they vary by day.

If you’d rather cover this same stretch of blocks one avenue over, the parallel Irving Place route from Union Square to Gramercy hits a different set of addresses worth comparing.

Getting Back

From 21st Street, it’s a short walk east to the 6 train at 23rd Street–Park Avenue South, or you can retrace the avenue back to the 14th Street hub. Either way, the whole corridor is compact enough to walk without much subway shuffling in between stops.

Frequently Asked Question

Is it faster to walk Park Avenue South or take the subway between these blocks?

Walking is faster for this specific corridor. The distance from 14th Street to 21st Street is under half a mile, about a 12 to 15 minute walk at a normal pace, and there’s no subway line built to cover that short a distance north-south along this stretch. The 6 train does stop at both 14th Street and 23rd Street, but by the time you’ve gone down to the platform, waited, and come back up, you’d likely have covered the same ground on foot. Save the subway for the ends of the trip, getting to 14th Street or leaving from 23rd, rather than for the middle of the walk.

Before You Go

Hours, menus, and reservation policies change more often than addresses do. Check each restaurant’s current listing before you head out, particularly for anything you’re planning around a specific seating time.

The Walk in Short

Eight blocks, one street name change, and a run of Italian kitchens that range from a fast panino counter to a tasting-menu splurge. Whether you’re starting at Union Square or working down from Gramercy Park, Park Avenue South gives you a clear line to walk and a reasonable spread of options along it. Check current hours and menus for each stop before you commit to a plan.

Editor’s note: Isabelle’s Osteria is affiliated with this publication. Restaurants were selected using the criteria described above.