Hallowell Weekend Preview: Feb 20–23, 2026

Written By Lori Hayes

This weekend, Hallowell offers two distinct ways to experience downtown. Whether you are looking for the refined "Daycrawler" experience—dinner music and art—or the high-energy "After Dark" scene, here is your organized guide to the weekend.

Top Pick: The "Must-See" Event

Gaslight Theater: "Things My Mother Taught Me" Katherine DiSavino’s sentimental comedy follows a young couple moving into their first apartment in Chicago, only to be descended upon by both sets of parents. It’s a hilarious and touching look at generational lessons and family bonds.

  • Where: Hallowell City Hall, 1 Winthrop St.

  • When: Friday & Saturday at 7:30 PM, Sunday at 2:00 PM

The Daycrawler’s Guide

For those who appreciate an elegant meal, a quiet gallery, and a full night's sleep.

Friday, Feb 20

  • Lee Sykes | Slate’s Restaurant, 5:30 PM – 8:00 PM. Intimate dinner music at one of the region's premier dining destinations.

  • Nat Hussey | The Quarry Tap Room, 5:00 PM – 8:00 PM.

Saturday, Feb 21

  • Wine & Cheese Tasting | Uncorked Wine & Cheese, 3:00 PM – 6:00 PM. Bank from Nappi Distributors will be showcasing an excellent selection of wine.

  • Katie Daggett | Slate’s Restaurant, 5:30 PM – 8:00 PM.

  • Chris & Dave Gagne | The Quarry Tap Room, 5:00 PM – 8:00 PM.

Monday, Feb 23

Ongoing Art (Gallery Hours)

  • Local Collective Art | The Blanchard Gallery. Featuring works by Wendy Larson, Chris Cart, Deborah Train, Bia Winter, Marc Poirier, Nancy Nicol, and more.

  • Brittany Cates | Michel Paul Artist Studio. Resident artist for February.

Water Street After Dark

For the high-energy crowd looking for late-night lounges and the full downtown vibe.

Friday Night

Saturday Night

Sunday Night

Lori Hayes
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