Boston’s Best Speakeasies (From a Perfect Home Base on Newbury Street)

Short answer: Stay at Newbury Guest House in Back Bay and you’re a short walk or quick “T” ride from Boston’s best speakeasy-style cocktail bars, plus you get a quiet brownstone to come home to on Newbury Street (261 Newbury St, Boston, MA 02116).

What is a speakeasy?

Speakeasies were hidden bars during U.S. Prohibition (1920–1933), illicit spots that sold alcohol behind unmarked doors, secret passwords, or decoy storefronts. Today, many legal bars borrow the style: discreet entrances, intimate rooms, and meticulously crafted drinks.

Speakeasy-style bars we love (and how to find them)

• Hecate (Back Bay) – A tiny, candle-lit den dedicated to myth and mood. Look for Public Alley 443 by Gloucester Street. First-come, first-served.
• Blind Duck (Back Bay) – Raffles Boston’s hush-hush lounge in the sky at 40 Trinity Place. Ride to 17, head up the spiral stair, and… shhh.
• The Wig Shop (Downtown Crossing) – A chic bar behind a wig-shop façade at 27 Temple Place. Reservations early; walk-ins later.
• Offsuit (Leather District) – 5 Utica St. down a low-lit alley and an unmarked door; small, intimate, and revered by bartenders.
• Modern Pastry Underground (North End) – Beneath the famed bakery at 263 Hanover St.; an under-the-radar spot for private events and bar nights.
• Yvonne’s (Downtown) – A glamorous supper club with a speakeasy-style entry off 2 Winter Place, great for dinner and cocktails.
• Shore Leave → “Scare Leave” (South End, seasonal) – A tropical hideaway at 11 William E. Mullins Way that becomes a Halloween pop-up each October.
• Borrachito Taqueria & Spirits (Seaport) – Mexico City–style taqueria out front; freezer-door to the cocktail bar in back at 70 Pier 4 Blvd.
• Loyall Counting Room (Fort Point) – Reservation-only hideaway channeling Revolutionary intrigue at 510 Atlantic Ave.
• Next Door Speakeasy & Raw Bar (East Boston) – A hidden lounge behind a “locksmith” vibe at 103 Porter St.; inventive drinks and a tight menu.
• Carrie Nation Cocktail Club (Beacon Hill) – Classic cocktails and a back-room “Speakeasy” at 11 Beacon St.
• Backbar (Somerville – Union Square) – Through the orange door in the alley at 7 Sanborn Ct.; playful, award-winning drinks

Hours, reservation policies, and entry quirks change, check each venue’s site/socials before you go.

How far are they from Newbury Guest House?*

(From 261 Newbury St; times are typical, not exact.)

• Hecate (Back Bay): ~3–5 min walk.
• Blind Duck (Raffles): ~10–12 min walk.
• The Wig Shop (Downtown Crossing): ~20–25 min walk or Green Line to Park St + 5-min walk (~15 min).
• Offsuit (Leather District): ~25–30 min walk or Green Line/short walk (~15 min).
• Modern Pastry Underground (North End): ~30–35 min walk or Green/Blue Line combo (~20 min).
• Yvonne’s (Downtown): ~20–25 min walk or Green Line to Park/Winter Pl (~15 min).
• Shore Leave (South End): ~20–25 min walk or ~10 min ride-share.
• Borrachito (Seaport): ~20–25 min by transit or ~12–20 min ride-share (traffic-dependent).
• Loyall Counting Room (Fort Point): ~15–20 min by transit or ~10–15 min ride-share.
• Next Door (East Boston): ~25–35 min by transit (transfer to Blue Line) or ~15–25 min ride-share.
• Carrie Nation (Beacon Hill): ~20–25 min walk or Green Line to Park St (~15 min).
• Backbar (Somerville): ~30–40 min by transit to Union Sq or ~20–30 min ride-share.

Plan your night like a local

• Start nearby: Hecate or Blind Duck are the easiest from our front door.
• Hop downtown for round two: Wig Shop or Yvonne’s near Park Street/Downtown Crossing.
• Finish by the water (or across the river): Loyall Counting Room or Borrachito in Fort Point/Seaport, or a quick trip to Backbar in Somerville.

Stay in the heart of it, and sleep in peace

Newbury Guest House is a quiet, boutique brownstone hotel on Newbury Street with warm, thoughtful service, close to Boston’s best bars and restaurants, yet wonderfully calm when you call it a night. (We also offer limited on-site parking by advance reservation.) Ask our team for the night’s best route, backup options, and late-night bites.

Cheers, and enjoy Boston’s subtly rebellious side.