Brooklyn / Williamsburg
Williamsburg
Bar Crawl
Five stops up the Bedford–Berry spine — oysters and absinthe to a honky-tonk to the Manhattan skyline from 22 floors up.
Williamsburg is a night neighborhood — start around 5pm to catch The Bedford’s weekday mini-martini happy hour (4–7pm) and time the Westlight rooftop for sunset. Most deals here are weekday-only, and Maison Premiere’s famous $1 oyster hour isn’t currently running.
- 5 stops
- ~1 mi total walk
- $8 mini-martinis 4–7pm
- finish 22 floors up
The short version
- StartMaison Premiere – oysters and absinthe in a marble-and-brass classic.
- Free musicSkinny Dennis – honky-tonk, 18 drafts, Willie’s Frozen Coffee.
- The dealThe Bedford – $8 mini-martinis, weekdays 4-7pm.
- FinishWestlight – the Manhattan skyline from 22 floors up.
- Total walk~19 minutes up the Bedford-Berry spine, Grand St to North 12th.
The best Williamsburg bar crawl is five stops up the Bedford–Berry spine, about a mile and twenty minutes of walking: open with oysters and a martini at Maison Premiere (298 Bedford), cross to the honky-tonk Skinny Dennis, catch the $8 mini-martini happy hour at The Bedford, drop into the candlelit Hotel Delmano for a proper cocktail, and finish 22 floors up at Westlight with the Manhattan skyline in the glass. Go on a weekday from about 5pm to catch The Bedford’s 4–7pm deal and time the rooftop for sunset. Every bar was checked open in June 2026.
At a glance
The five stops in order, south to north up the Bedford–Berry spine — what to order, when to arrive, and the walk to the next.
| Stop | Bar | Order this | Arrive | Walk to next |
|---|---|---|---|---|
| 1 | Maison Premiere | A half-dozen oysters and a Sazerac | ~5:00pm | 5 min → |
| 2 | Skinny Dennis | A cheap draft and a Willie’s Frozen Coffee | ~5:45pm | 5 min → |
| 3 | The Bedford | Three $8 mini-martinis and the disco fries | ~6:30pm | 4 min → |
| 4 | Hotel Delmano | One well-made classic at the marble bar | ~7:30pm | 5 min → |
| 5 | Westlight | A cocktail by the glass at sunset | ~8:30pm | — last stop |
Map: the 5-stop route
The route runs up the Bedford–Berry corridor from Grand St to North 12th — off the L at Bedford Av, the G at Metropolitan, or the J/M/Z at Marcy Av.
Pins are numbered in walking order and joined by the gold route line – tap any pin for the order and directions.
The crawl, stop by stop
Walk it south to north up the Bedford–Berry spine. More options in our Williamsburg happy hour guide, and the full NYC bar crawls hub.
1 · Maison Premiere
Verdict: start with oysters and a martini, because nobody in Williamsburg does the old-world thing better. Maison Premiere is a marble-and-brass oyster-and-absinthe bar that looks like a New Orleans fever dream, with a back garden and one of the best cocktail programs in Brooklyn. Honest caveat: the famous $1 oyster happy hour isn’t running right now, so you’re paying full freight — but a half-dozen and a Sazerac at the bar is still the right way to open a crawl. The move: sit at the horseshoe bar, let the bartender steer the oysters, and don’t skip the absinthe service if you’ve got the night for it.
2 · Skinny Dennis
Verdict: the antidote to all that — a honky-tonk dive two blocks over where the live country starts early and barely stops. Named for a 6-foot-11 bassist, Skinny Dennis pours 18 drafts, runs a vintage jukebox, and serves Willie’s Frozen Coffee, a boozy frozen number that’s basically a Williamsburg rite of passage. No cover, no pretense, a band most nights. The move: a cheap beer, a Willie’s, and a spot near the band. Honest caveat: it’s small and gets packed when there’s a good act on, so go early or be ready to wedge in.
3 · The Bedford
Verdict: the deal stop, and the one to time. The Bedford — Williamsburg’s original gastropub, right by the Bedford Av L (not to be confused with the newer Bedford on Stone Street downtown) — runs a weekday happy hour, 4–7pm, built around an $8 mini-martini menu: dirty, espresso, mezcal, saffron vesper, peach. Beer’s $6, wine $9–10, and the food (seaweed-butter focaccia, Greek disco fries) is better than it needs to be. The local move: order three mini-martinis, share the disco fries, and you’re out forty bucks lighter and grinning. Honest caveat: the deal’s weekdays only, so a weekend crawl pays full price here.
thebedford.nyc · See our best cocktail bars in NYC
4 · Hotel Delmano
Verdict: the craft peak — a candlelit, no-sign speakeasy on Berry that’s been one of Brooklyn’s prettiest cocktail rooms for over a decade. A curved marble bar, antique mirrors, a seasonal menu of original cocktails and a 100-bottle wine list, plus a proper raw bar if you want more oysters. No happy hour; this is a sit-and-savor stop. The move: a seat at the marble bar, one well-made classic, and the hush of the back room. Honest caveat: it doesn’t open till 4pm (2pm weekends) and fills up — and with no sign out front, look for the door at Berry and North 9th.
hoteldelmano.com · See our best wine bars in NYC
5 · Westlight
Verdict: finish 22 floors up with the whole Manhattan skyline in the window. Westlight, atop the William Vale, is the rooftop that earns the cliché — 360-degree views, Andrew Carmellini small plates, and a heated terrace that works year-round. There’s no happy hour, so cocktails run $19–$25; you’re paying for the view, and on a clear night it’s worth it once. The move: time your arrival for sunset or full dark, get a spot by the glass, and split small plates. Honest caveat: it’s reservations-smart on weekends and the priciest stop by far — end here, don’t start here.
westlightnyc.com · See our more Williamsburg spots
Williamsburg bar crawl: FAQ
What’s the best bar crawl route in Williamsburg?
Five stops up the Bedford-Berry spine, about a mile of walking: start with oysters and a martini at Maison Premiere (298 Bedford Ave), then the honky-tonk Skinny Dennis, The Bedford for $8 mini-martinis, the candlelit Hotel Delmano for a proper cocktail, and finish 22 floors up at Westlight with the Manhattan skyline.
When should I do the Williamsburg bar crawl?
Go on a weekday and start around 5pm. That catches The Bedford’s mini-martini happy hour (4-7pm, weekdays only) and lets you time the Westlight rooftop for sunset. Most Williamsburg happy hours are weekday-only, so a weekend crawl pays full price at most of these rooms.
How long is the Williamsburg bar crawl?
About a mile and 19 minutes of walking total, running south to north from Grand Street up to North 12th. With five stops it’s a comfortable three-to-four-hour night. Maison Premiere, Hotel Delmano, and Union Pool all run till 1-2am if you want to keep going.
Where can I get oysters on a Williamsburg crawl?
Maison Premiere is the oyster anchor, though its famous $1 happy hour isn’t currently running, so it’s full price. Hotel Delmano has a strong raw bar too. For cheap oyster happy hours nearby, Layla ($2 oysters, Bedford Ave) and Lighthouse BK ($1 oysters daily until 6pm) run cheap oyster deals – Maracuja no longer serves food – see our Williamsburg happy hour guide.
Is Westlight worth it without a happy hour?
For the view, once. Westlight has no happy hour and cocktails run $19-25, but it’s 22 floors up with a 360-degree Manhattan skyline view and a heated year-round terrace. End the crawl there at sunset or full dark; don’t start there, and don’t expect a deal.
Last updated: June 2026. Deals and hours change – confirm with the venue before you go. Spot something out of date? Let us know.