Destinations / New York City / Top Things to Do in New York City for Speakeasy Fans on the Upper West Side
Top Things to Do in New York City for Speakeasy Fans on the Upper West Side
1. The Owl’s Tail
A cozy cocktail parlor steps from the Beacon Theatre, The Owl’s Tail channels a speakeasy spirit with velvet banquettes, low light, and seasonally driven classics shaken and stirred behind a bustling L‑shaped bar.
✓ Why Go:
It’s an intimate, craft‑forward refuge where bartenders tailor Prohibition‑era staples to your palate before or after a show.
✓ Best Time to Visit:
Early evening on weekdays or post‑show after 10pm for a mellower crowd.
✓ Insider Tip:
Nab a corner banquette and ask for a spirit‑forward riff on a Boulevardier or Martini—the team does off‑menu classics well.
✓ What Visitors Say:
Guests rave about the warm neighborhood feel, balanced cocktails, and date‑night ambience; expect a wait at peak pre‑show hours.
2. The Dead Poet
A narrow, mahogany‑lined literary pub where signature cocktails salute famous writers—think speakeasy mood, Irish hospitality, and late hours.
✓ Why Go:
For strong classics, witty menu nods, and a snug, old‑New‑York vibe that feels hidden in plain sight.
✓ Best Time to Visit:
Late night after 11pm (it’s open until 4am) or weekday afternoons for easy seating.
✓ Insider Tip:
Grab a bar stool to watch the pour and ask for their namesake cocktail tailored to your base spirit.
✓ What Visitors Say:
Beloved as a neighborhood staple with welcoming bartenders; space is tight, which adds charm and crowds.
3. Caledonia Bar
A dim, whisky‑centric den with shelves of Scotch and global drams, ideal for speakeasy fans who prize neat pours and quiet conversation.
✓ Why Go:
Curated flights and knowledgeable staff make it a smart stop for exploring classic brown spirits.
✓ Best Time to Visit:
Weeknights 5–8pm for flights without a rush.
✓ Insider Tip:
Ask for a custom three‑pour Scotch flight that progresses from light and floral to peaty and smoky.
✓ What Visitors Say:
Regulars praise the selection and understated vibe; a go‑to when you want substance over scene.
4. Nobody Told Me
A sleek cocktail hideaway near 106th Street where inventive drinks meet chef‑y small plates—dark, intimate, and mixology‑driven.
✓ Why Go:
Playful signatures and polished classics make it a north‑UWS standout for serious cocktail lovers.
✓ Best Time to Visit:
Late night after 10pm or weekday lunch‑to‑happy hour when the bar is chatty and unhurried.
✓ Insider Tip:
Sit at the bar and ask for a stirred, spirit‑forward off‑menu riff if you like boozy, balanced profiles.
✓ What Visitors Say:
Praised for creative drinks and chic yet friendly service; can be lively during prime hours.
5. Smoke Jazz & Supper Club
A candlelit jazz room with ruby curtains and a classic bar, Smoke delivers supper‑club intimacy—perfect for those who love speakeasy ambiance with live music.
✓ Why Go:
Top‑tier jazz in a moody setting pairs beautifully with whiskey and classic cocktails.
✓ Best Time to Visit:
Late set or weeknights for a more relaxed, romantic vibe; reserve ahead if you want a table.
✓ Insider Tip:
Solo? Try for a bar seat just before the late show—often the quickest path inside.
✓ What Visitors Say:
Fans call it a quintessential NYC jazz night—intimate, polished, and worth planning for.
6. Shalel Lounge
Slip down candle‑strewn stairs to a grotto‑like Mediterranean lounge with alcoves and nooks—romance, low light, and cocktails made for lingering.
✓ Why Go:
It’s the UWS’s subterranean escape with a hidden‑away feel, ideal for speakeasy‑style privacy.
✓ Best Time to Visit:
Late evening on Thu–Sat or Sunday nights for a quieter cap to the weekend.
✓ Insider Tip:
Ask for a back‑room two‑top and order a classic like a Sidecar alongside mezze to share.
✓ What Visitors Say:
Loved for its cozy hideaway atmosphere; seating is limited, so patience pays off.
7. Arthouse Bar
A lobby bar with 1920s touches, live music on select nights, and cocktails inspired by speakeasies and Harlem music clubs—vintage without the velvet rope.
✓ Why Go:
Classic drinks, comfy lounges, and occasional jazz make it a low‑key Prohibition‑style hang.
✓ Best Time to Visit:
Happy hour Mon–Fri 5–7pm or early evening before Lincoln Center performances.
✓ Insider Tip:
If available, request seating in the Library space for peak old‑New‑York ambience.
✓ What Visitors Say:
Visitors appreciate the relaxed elegance and live tunes; service is friendly, atmosphere unpretentious.
8. Dizzy’s Club
Jazz at Lincoln Center’s intimate club pairs skyline views with classic cocktails—a sophisticated nod to the supper‑club era at the southern edge of the UWS.
✓ Why Go:
World‑class jazz in a refined room that still feels like a late‑night hideout.
✓ Best Time to Visit:
Thu–Sat Late Night Session around 10:45pm for an atmospheric, less formal experience.
✓ Insider Tip:
Arrive early for the late set; walk‑up tickets are limited and prime bar seats go fast.
✓ What Visitors Say:
Lauded for impeccable sound and city views—memorable for music lovers and cocktail fans alike.
9. Ashford & Simpson’s Sugar Bar
A soulful Upper West Side supper club where live R&B, jazz, and open‑mic nights evoke Harlem Renaissance energy—dimly lit, intimate, and celebratory.
✓ Why Go:
For a music‑soaked evening with classic cocktails and the feel of a community salon.
✓ Best Time to Visit:
Thursday open‑mic nights or weekend evenings for full energy and surprise cameos.
✓ Insider Tip:
Reserve early for performance nights; bar perches offer great sightlines without committing to a full dinner.
✓ What Visitors Say:
Guests love the welcoming vibe and live music; service hums once the show starts.
10. The Leopard at des Artistes
An art‑filled landmark with restored 1920s murals and a polished bar—order a Martini under Howard Chandler Christy’s nymphs and channel golden‑age glamour.
✓ Why Go:
It’s old‑world elegance on the UWS, perfect for speakeasy traditionalists who favor classic cocktails in storied rooms.
✓ Best Time to Visit:
Late dinner drinks after Lincoln Center or jazz brunch for music with your tipple.
✓ Insider Tip:
Slide into a bar seat for swift service and a textbook Manhattan before a stroll along Central Park West.
✓ What Visitors Say:
Admired for timeless ambience, gracious service, and precisely made classics—an Upper West Side icon.
