Destinations / New York City / Top Things to Do in New York City for Speakeasy Fans on the Upper East Side
Top Things to Do in New York City for Speakeasy Fans on the Upper East Side
1. UES.
Behind a working ice-cream counter on Second Avenue, a secret door of stacked “pint cartons” opens into a neon-kissed cocktail den stocked with uptown-themed drinks and cheeky, Roaring ’20s flourishes.
✓ Why Go:
It’s the UES’s quintessential speakeasy moment—fun reveal, strict(ish) dress code, and serious mixology—without leaving the neighborhood.
✓ Best Time to Visit:
Weeknights 6:30–8:00 pm for a smooth entry; on Fri–Sat arrive before 7:30 pm or after 11:00 pm to cut the line.
✓ Insider Tip:
Ask to see “the storage room” at the counter; cocktail attire is enforced and boozy desserts go fast—order one with your first round.
✓ What Visitors Say:
Guests rave about the hidden-door reveal, polished service, and Instagram-ready drinks; expect occasional waits and a dressy crowd.
2. Keys & Heels
A locksmith-and-shoe-repair storefront conceals a velvet-lined lounge pouring photogenic, fruit-forward cocktails under moody lights and a playful DJ soundtrack.
✓ Why Go:
Theatrical entrance plus lively late-night energy scratch the classic speakeasy itch—right on Second Avenue.
✓ Best Time to Visit:
Thu–Sat 9:30–11:00 pm for peak vibe; arrive by 8:00 pm if you want a seated corner.
✓ Insider Tip:
Weekend reservations often drop on Tuesdays at noon; watch socials for occasional magic-night pop-ups and special sets.
✓ What Visitors Say:
People love the surprise façade and balanced cocktails; it can get loud and lines form at prime time.
3. Sugar East
Descend a narrow staircase on First Avenue into a mid‑century Havana–meets–Mad Men lounge of leather banquettes, low lights, and DJ‑driven nights.
✓ Why Go:
A sultry, subterranean speakeasy vibe with well-executed house cocktails and late-night energy—ideal for a date or a nightcap.
✓ Best Time to Visit:
Thu–Sat after 10:00 pm for DJs and a buzz; weekdays 7:00–9:00 pm for conversation-friendly sipping.
✓ Insider Tip:
The entrance is between 61st and 62nd Streets; request a booth and try a signature like Coconut or Celery if it’s on the menu.
✓ What Visitors Say:
Praised for atmosphere and service; some note it’s darker and music-forward—part of the charm for night owls.
4. Bemelmans Bar
Inside The Carlyle, murals by Madeline’s Ludwig Bemelmans glow over tuxedoed bartenders and nightly live music—New York’s most storied cocktail room.
✓ Why Go:
Old New York elegance for speakeasy devotees who love history, perfect martinis, and a piano that swings into a late trio.
✓ Best Time to Visit:
Early evening before the pianist starts or late after 10:00 pm to minimize waits; weekends fill quickly.
✓ Insider Tip:
A cover charge applies once music begins and a smart dress standard is observed—bar seats turn over fastest.
✓ What Visitors Say:
Universally adored for its magic and music; expect premium prices and a line that’s part of the ritual.
5. Brandy's Piano Bar
A tiny, time-capsule piano bar where singing bartenders lead show tunes and classics to a packed, joyful room until the wee hours.
✓ Why Go:
It channels Prohibition‑era conviviality—shoulder‑to‑shoulder singalongs, strong pours, and the kind of community vibe speakeasy fans treasure.
✓ Best Time to Visit:
Weeknights around 9:30 pm for the first sets; on weekends, line up by 9:00 pm for space near the piano.
✓ Insider Tip:
Two‑drink minimum and no reservations—bring cash for the tip bucket and arrive early to snag a seat.
✓ What Visitors Say:
Beloved neighborhood staple; lively, crowded, and unforgettable when the room belts together.
6. Melody's Piano Bar
A polished art‑deco salon with a working fireplace, nightly piano and jazz, and a martini‑centric cocktail list—UES glamour without pretense.
✓ Why Go:
For a refined, live‑music night that feels like a classy cousin to downtown speakeasies—perfect for dates or dress‑up group hangs.
✓ Best Time to Visit:
7:00–10:00 pm for piano sets; late night on weekends for a spirited crowd without losing elegance.
✓ Insider Tip:
Walk‑ins only; a music charge typically applies after 7:00 pm—order a classic martini or ask for the bartender’s riff.
✓ What Visitors Say:
Guests gush over the room’s look and the musicianship; it’s popular, so short waits are common at peak hours.
7. The Drunken Munkey
Old‑Bombay nostalgia meets a serious “East India” cocktail program—vintage glassware, spice‑laced classics, and a cozy bar wrapped around an open kitchen.
✓ Why Go:
Transportive décor and historically rooted cocktails make it catnip for speakeasy fans who love craft and story in equal measure.
✓ Best Time to Visit:
Early evening 5:30–7:30 pm for bar seats; later for dimly lit date‑night vibes.
✓ Insider Tip:
Reserve for tables; solo or duo? Ask for bar seats and pair a classic (Pimm’s or Sazerac riff) with small plates.
✓ What Visitors Say:
Highly rated for balanced cocktails and hospitable service; space is intimate and fills quickly.
8. The Penrose
A reclaimed‑wood gastropub with vintage wallpaper, proper classics, and a bustling front bar that brings downtown cocktail culture uptown.
✓ Why Go:
Reliable drinks, a lively scene, and late hours—ideal as a first stop before a hidden bar, or the night’s mainstay.
✓ Best Time to Visit:
Weekend afternoons for a mellow cocktail brunch; after 11:00 pm for easier bar space.
✓ Insider Tip:
Post up by the front curve of the bar for quickest service; bartender’s‑choice classics are on point.
✓ What Visitors Say:
A crowd‑pleasing staple—friendly staff, consistent pours; noise swells during peak weekend hours.
9. The Auction House
Velvet drapes, candlelight, and a fireplace set the stage for an intimate salon that feels like a whisper‑quiet, speakeasy‑adjacent hideaway.
✓ Why Go:
A romantic lounge for low‑key cocktails and conversation when you want vintage ambiance without the crowds.
✓ Best Time to Visit:
Fri–Sat after 10:00 pm for the sultry mood; midweek evenings for hush‑hush dates.
✓ Insider Tip:
Dress nicely; there’s a 25+ door policy on weekends and you’ll order at the bar (no table service).
✓ What Visitors Say:
Regulars praise the cozy room and relaxed pacing; music volume and vibe can vary by night.
10. Caledonia Scottish Pub
A wood‑paneled whisky haven with a deep selection and knowledgeable bartenders who build custom flights in an intimate, low‑lit room.
✓ Why Go:
For spirit‑first speakeasy fans, it’s a master class in Scotch and world whiskies—perfect for a contemplative nightcap.
✓ Best Time to Visit:
Weeknights 7:00–9:00 pm for tastings and talk; late Friday for a civilized close to the night.
✓ Insider Tip:
Ask for a region‑by‑region Scotch flight and inquire about monthly tasting nights—they’re laid‑back and educational.
✓ What Visitors Say:
Loved for its warm welcome and breadth of bottles; tiny room, so it fills fast at peak hours.
