Cast of Shrek the Musical in full costume and makeup at the Montclair Theater Festival at Brookdale Park

Things to Do in Montclair This Weekend: Montclair Flea, Theater in the Park, Comedy and More

Camila Gonzalez July 21, 2026

It’s a big weekend for outdoor and live performance. The Montclair Theater Festival brings free Shakespeare and Seussical to Brookdale Park on Saturday, the Montclair Flea runs both days at Lackawanna Station, and there’s comedy, D&D and a sip-and-paint to fill out the schedule. Here’s what’s on July 24 through 26.

Collective Comedy Festival at Studio Playhouse

Thursday, July 23 through Saturday, July 25 | Tierney’s Tavern and Studio Playhouse | Tickets required

Collective Comedy’s annual festival spans three nights and two Montclair venues. Night 1 is Thursday at Tierney’s Tavern, 138 Valley Road, with Tristan Bowling headlining; the youngest Golden Ticket winner in Kill Tony history, Bowling is a fixture of the GAS Digital Network. Doors open at 8 p.m., showtime at 8:30 p.m. Night 2 moves to Studio Playhouse, 14 Alvin Place, on Friday, July 24, with Brendan Sagalow of the Comedy Cellar headlining; doors at 8:30 p.m., showtime at 9 p.m. Night 3 is Saturday at Studio Playhouse with a showcase featuring Mike Recine, KP Burke and more, starting at 8 p.m. Free parking at both venues. 

D&D One-Shot at Eclectic Chic Boutique

Friday, July 24, 7 to 9 p.m. | Eclectic Chic Boutique | Free

Eclectic Chic Boutique is hosting a one-shot Dungeons & Dragons campaign Friday evening, and no prior experience is needed. The scenario is Heist Heist Baby!, set in the city of Waterdeep, where players are assembled by a shadowy criminal to steal a priceless blue diamond called the Heart of Ice. The evening is designed to be silly and low-stakes, and the organizers explicitly welcome LGBTQIA+ players, neurodiverse players and anyone who has never touched a d20. Ages 16 and up. 

Sip & Paint: Moonlit Beach Haze at Wine & Design

Friday, July 24, 8 p.m. | Wine & Design, 1 Greenwood Ave., Suite 101 | $42

Wine & Design’s Montclair studio runs guided painting classes set to music, and this Friday’s session features a moonlit beach scene. All canvases come pre-sketched, so the focus is on painting rather than drawing from scratch. BYOB, wine glasses and opener provided; no hard liquor. Doors open 15 minutes before start time. Ages 16 and up; 21 and up to drink. Free parking in the studio lot off Glenridge Avenue. 

Montclair Theater Festival at Brookdale Park

Saturday, July 25, 2 to 8 p.m. | Brookdale Park, Bloomfield | Free

Vanguard Theater Company brings its second annual outdoor theater festival to Brookdale Park this Saturday, with six hours of free programming for all ages. The mainstage features abridged professional productions of Seussical the Musical and Shakespeare’s The Tempest, continuing the company’s Shakespeare in the Park tradition. Throughout the afternoon, more than 20 New Jersey theater companies will perform in pop-up spots throughout the park, alongside food trucks, artisan vendors and hands-on activities. Last year’s inaugural festival drew more than 2,000 attendees and earned an official Montclair Theater Day proclamation from both Essex County and Montclair Township. Free parking on site. 

Montclair Flea at Lackawanna Station

Saturday, July 25 and Sunday, July 26, 11 a.m. to 5 p.m. | Lackawanna Station, 1 Lackawanna Plaza | Free

Montclair Flea holds its markets at Lackawanna Station on the third Saturday and Sunday of every month, from 11 a.m. to 5 p.m., inside the 34,000-square-foot Big Room, making it one of the largest indoor flea markets in New Jersey. This weekend’s market brings the usual rotating mix of handmade goods, vintage finds, art, jewelry and specialty food, fully indoors regardless of weather. 

For the full list of upcoming events in Montclair, visit montclairpod.com/events.

Image credit: Vanguard Theater Company

Camila is a journalist and writer whose work spans reporting, storytelling and digital content. She contributes to The Montclair Pod with a focus on the people, places and issues that define community life.

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