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Off-Season Restaurants in Provincetown: The Painted Lady

Painted Lady, a standout Provincetown pop-up at Local 186, delivers refined yet unpretentious dishes—think Sicilian stuffed squid, braised oxtail, and expertly crafted cocktails. One of the best dining experiences in Provincetown this (off)season, Painted Lady Pop-Up at Local 186, Provincetown.
Provincetown
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A picture of the paper menu for The Painted Lady pop-up restaurant at Local 186 in Provincetown, MA. The menu is on a small clipboard and the top of the paper is held to the board by a spring loaded clamp at the top.

Painted Lady Pop-Up at Local 186, Provincetown

  • What is it? A limited-time pop-up at Local 186 showcasing refined, confident cuisine.
  • What’s on the menu? Elevated small and large plates, including Sicilian Stuffed Squid, Braised Oxtail, Duck Confit, and handcrafted cocktails like the Prickly Lady.
  • Is it worth it? Absolutely. Thoughtful dishes, warm ambiance, and standout flavors make this one of Provincetown’s best dining experiences.
  • How long will it be open? Currently running Friday–Tuesday from 5 PM until close (check Local 186 for updates).
  • Best dish to order? The Braised Oxtail—rich, tender, deeply satisfying.
  • When is it open? Fri-Tues: 5p-close

On the table tonight:

  • Sicilian Stuffed Squid
  • Miso Butter Onions
  • Cacio e Pepe
  • Spaetzle & Sausage
  • Duck Confit
  • Rib Eye
  • Braised Oxtail
  • Prickly Lady
  • Lychee Saketini
  • 2 delicious desserts

Stepping into the hall, they were hypnotized from the first. Out of the frigid cold, the warm enveloped them like the devil’s purse. There were mirrors and a clock and more mirrors and so much brown. The lighting dimmed down, the frames were all sharp, ornate, a worthy crown.

The dining room was around the corner to the right (it was two rights, really), facing the window that opened to the table, in bloom - they were in for a night at the first kick of mushrooms. One fell onto the corner chair, barely salvaging themselves from full repose; the other of this first two then chose. Worth a mention that this foursome would stagger in like hoboes.

The Painted Lady @ Local 186

The Painted Lady pop-up at Local 186 is an exceptional dining experience—each course precise, deliberate, and composed with intention. From the first sip of a drink to the final bite of dessert, the execution is confident, unhurried, assured.

We began with cocktails: the Prickly Lady, its mezcal base carrying the familiar wisp of woodsmoke; the Lychee Saketini, a cooling, floral counterpoint; and a third, its name now lost in the ebb of the evening, but one we ordered twice. The bar hummed, its patrons engaged but never intrusive, the room steeped in a convivial ease that only Provincetown, in its best moments, manages to conjure.

The Painted Lady @ Local 186
The Painted Lady @ Local 186
The Painted Lady @ Local 186

The first plates arrived, small.

Sicilian Stuffed Squid

The Painted Lady @ Local 186: Sicilian Stuffed Squid

Tender, yielding, its pesto filling a textural contrast both lush and substantial.

Miso Butter Onions

The Painted Lady @ Local 186: Miso Butter Onions

A dish simple in title but wholly absorbing, the softened sweetness of the onions enriched by umami depth, the accompanying bread essential for balance.

Cacio e Pepe

The Painted Lady @ Local 186: Cacio e Pepe

Restrained yet decadent, coaxing complexity from elemental ingredients. If a critique must be made, it is only that the portions—designed for three—left our table of four in a quiet negotiation of shares. The service, otherwise attentive, could have anticipated this.

Then the large plates.

Spaetzle and Sausage

The Painted Lady @ Local 186: Spaetzle and Sausage

Abundant and richly textured, its brussels sprouts and pomegranate lending a subtle interplay of earth and brightness.

Rib Eye

The Painted Lady @ Local 186: Rib Eye

Perhaps sliced a touch thinner than anticipated, but masterfully charred, draped in melting garlic butter and crowned with rosemary, a heap of fries standing at attention beside it.

Duck Confit

The Painted Lady @ Local 186: Duck Confit

Bronzed and supple, resting in a port-fig reduction, its accompanying potatoes crisp and golden.

Braised Oxtail

The Painted Lady @ Local 186: Braised Oxtail

Deeply savory, collapsing at the mere suggestion of a fork, summoning memories of Harlem and late nights spent recklessly clearing and sucking at these very same bones.

For Dessert ...

A fleeting, bittersweet regret: the exact menu eluded us, leaving us only with what remained—an image, a taste.

The Painted Lady @ Local 186: Mystery Lemon Dessert

A lemon-something, sharp and cleansing.

The Painted Lady @ Local 186: Mystery Ice Cream & Soft Cookie Dessert

A plate of unexpectedly tender cookies alongside ice cream, steering away from brittle refinement toward something simpler, softer, more indulgent.

A meal at Painted Lady lingers. Not only for its flavor or composition, but for its sense of place—an experience unhurried, immersive, momentary yet indelible.

•••••

She steadied her palms on the table, stood up entirely too soon. It was a wobbly walk, a headshaking putter, down the short hall into the bathroom. She locked the door and enjoyed a minor reprieve; leaned her head back against the wall and soaked the sweat from her upper lip into the cuff of her sweater’s sleeve. Maybe she’d never leave, maybe reached her tomb. The boom of the shroom and the pow of the wow in her eyes were on a spiraling weave. Her mouth was like cotton, her belly was now rotten and the rotten was lurching to heave. “Get back,” she sweated and pulled the cool air into her head, cocked back and wedged on the door. The next she remembered was blinking and pulling her cheek from the sticky tile floor. The walk to the table - please, no way she’s able - was beyond an unmentionable chore. To piss, she dreamed, to piss and get back to the miso onions and chair steadily holdin her ass to the flat of the floor. Water was savior, water was life, water and water some more.

The Painted Lady @ Local 186

•••••

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