Midtown Bar Crawl: A Bryant Park Loop on Happy Hour

The route, stop by stop

1. 

   1. LOLITA Midtown

   Cocktails (Lolita Margarita, Paloma, Daiquiri, Mezcal Negroni, Dark & Stormy) $12 · House vinos (red, white, bubbles) $11
   Daily 3pm–6pm · Daily 10pm–12am · 45 W 45th St · 47th–50th Streets–Rockefeller Center (B, D, F, M)

   Start at Lolita, a Mexican bar at 45 West 45th Street. Its happy hour runs every day from mid-afternoon to early evening and comes back late at night, and the afternoon window is the first on this route to end, so it leads. The list covers house cocktails such as the Lolita margarita, paloma, daiquiri and mezcal negroni, plus house wines, cervezas and discounted bites. The Rockefeller Center station on the B, D, F and M is three minutes away.

   Deal checked Oct 23, 2026 on the bar's own site.

2. 1 min walk from LOLITA

   

   2. Valerie Midtown

   oysters $1
   Mon–Fri 4pm–7pm · 45 West 45th Street · 47th–50th Streets–Rockefeller Center (B, D, F, M)

   Valerie, a New American restaurant, shares Lolita's address, so stop two is a few steps away. Its happy hour runs Monday through Friday from late afternoon into the early evening, with oysters on the list and, per its own site, cocktails, house wines, draft beers and light bites. The restaurant says group happy hour bookings need a reservation, so book ahead if you are more than a few people.

   Deal checked Oct 19, 2026 on the bar's own site.

3. 6 min walk from Valerie

   

   3. The Dawson 39 Midtown

   House White Wine $9.28 · House Red Wine $9.28
   Mon–Fri 12pm–7pm · Sat 12pm–1am · Sun 12pm–11pm · 54 West 39th Street · 42nd Street–Bryant Park (7, B, D, F, M)

   Walk about six or seven minutes south to The Dawson 39, an Irish pub and restaurant on West 39th Street. It has the longest weekday window of the five, from midday into the early evening, and it keeps a deal on weekends. The list is long: house wines and rose, Aperol and Hugo spritzes, bottled and draft beer, plus nachos, wings, hummus, pretzel bites and a mini charcuterie plate. Make it your food stop.

   Deal checked Oct 18, 2026 on the bar's own site.

4. 2 min walk from The Dawson 39

   

   4. Croton Reservoir Tavern Midtown

   Mango Habanero Margarita $12 · Classic Margarita $10
   Tue–Fri 4pm–8pm · 108 W 40th St · 42nd Street–Bryant Park (7, B, D, F, M)

   Croton Reservoir Tavern is two minutes away on West 40th Street, a minute from the 42nd Street-Bryant Park station. Its happy hour runs Tuesday through Friday from late afternoon into the evening, in The Speakeasy on the lower level; if that room is booked for a private event, the same deal moves upstairs. Margaritas, an Old Fashioned, a Manhattan, sangria, an Aperol spritz, select wines, draft beer and well drinks are all on it.

   Deal checked Oct 17, 2026 on the bar's own site.

5. 5 min walk from Croton Reservoir Tavern

   

   5. Jane Doe Bar & Restaurant Midtown

   Jane Doe Amber Ale $6
   Daily 11am–8pm · 12 W 44th St · 5th Avenue (7, B, D, F, M)

   Finish about five minutes north at Jane Doe Bar & Restaurant on West 44th Street. Its happy hour runs every day from late morning into the evening, so it is still on after most of the route has ended. The list starts with the house Jane Doe Amber Ale and adds bottled and draft beers, wine by the glass and mixed drinks. The 5th Avenue station is two minutes away.

   Deal checked Oct 23, 2026 on the bar's own site.

Which days the route works

Tuesday, Wednesday, Thursday and Friday are the days when all five stops run happy hour. Croton Reservoir Tavern is the limit: its deal starts on Tuesday, so on a Monday the route drops to four stops. Skip Croton and walk straight from The Dawson 39 to Jane Doe, which is still a short walk.

Weekends are thinner. Lolita and Jane Doe list happy hour every day and The Dawson 39 runs a weekend deal, but Valerie and Croton Reservoir Tavern are weekday only. A Saturday or Sunday version of three stops works, with The Dawson 39 as the anchor.

How to time it

The order follows the closing times. Lolita's afternoon deal ends first, so it leads. Valerie, at the same address, runs a little longer into the early evening. The Dawson 39 started its window at midday, so it is well underway when you arrive. Croton Reservoir Tavern and Jane Doe have the latest windows of the five, which is why they close out the loop.

If you arrive late, start at The Dawson 39 and do the last three stops. If you only have an hour after work, the Croton and Jane Doe pair is the safest choice, since both keep their prices into the evening.

Lolita gives you one more option. Its second window runs late at night, and Jane Doe is only about 120 meters away, so a late round back at the first stop is a two-minute walk from the last one.

The route, stop by stop

Lolita and Valerie share 45 West 45th Street, so the first leg is a few steps. From there the walk to The Dawson 39 on West 39th Street is the longest of the night, about 520 meters or six to seven minutes, heading south past the park. Croton Reservoir Tavern is about 170 meters away on West 40th Street, two minutes. The last leg is about 430 meters north to Jane Doe on West 44th Street, close to five and a half minutes.

In total, the loop is about 1.1 kilometers, or around 14 minutes of walking. Our distances are straight lines between bar coordinates at about 80 meters a minute, and Midtown crosswalks add time, so leave a little slack.

The mix is deliberate. Lolita brings margaritas and mezcal cocktails, Valerie brings oysters, The Dawson 39 brings the most food, Croton brings classic cocktails in a lower-level room, and Jane Doe brings a house ale for the last round.

Getting there by subway

Start from the 47th-50th Streets-Rockefeller Center station on the B, D, F and M, which our listing puts three minutes from Lolita and Valerie.

The middle of the loop sits by the 42nd Street-Bryant Park station, served by the 7, B, D, F and M: it is one minute from Croton Reservoir Tavern and two from The Dawson 39. Jane Doe, the final stop, is two minutes from the 5th Avenue station, so you finish within a short walk of the same lines you started on.

Happy hours near Bryant Park after work

Walking time is estimated from straight-line distance (about 80 m a minute). Up to 40 bars, closest first.

How we put this together

We chose the stops from our database of New York happy hours, which holds each bar's schedule and offers as listed on the bar's own website. The five bars on this route were last checked between October 17 and October 23, 2026, and the count of nearby happy hours was run on the same database on October 23, 2026. Walking times are straight-line distances between bar coordinates at about 80 meters per minute, so the real walk can be slightly longer. Subway stations and walking times come from each bar's listing.

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