Uptown Sound Music Fest sign at Anderson Park in Upper Montclair, NJ, listing the September 26 lineup including Waterbury Road, The Bard Band, El Ritmo and Rocking for Inclusion

What’s Happening in Montclair This Weekend: Uptown Sound Fest, Oktoberfest, a Flower Show and More

Camila Gonzalez September 23, 2026

Saturday, September 26 is one of the busiest days Montclair has seen all year. The first Uptown Sound Music Festival takes over Anderson Park in the afternoon, the Montclair History Center hosts its Fall Fest, Montclair Flea is at Lackawanna Station, Oktoberfest runs all day at Montclair Brewery and the Garden Club of Montclair’s centennial flower show continues at Van Vleck House & Gardens. Sunday brings the Montclair Dance Festival to the Wellmont Arts Plaza, and Friday kicks things off with a happy hour pop-up at RecRoom. Here’s what’s worth your time September 25 through 27.

Uptown Sound Music Festival at Anderson Park

Saturday, October 3, 2 to 8 p.m. | Anderson Park, Bellevue and North Mountain avenues, Upper Montclair | Free

Uptown Sound, a Montclair-based nonprofit built around celebrating local music and supporting small businesses, holds its first Uptown Sound Music Festival at Anderson Park on Saturday. What started as Dan & Day’s Music Festival has grown into a full afternoon of live music. The lineup opens at 2 p.m. with Rocking for Inclusion, followed by Latin ensemble El Ritmo from 3:20 to 4:35 p.m. and local favorite The Bard Band from 5 to 5:45 p.m. If you listen to the Pod, you already know the guy on keys (hint: it rhymes with “bike Schreiber”). The band, wisely, does not let him near a microphone. Headliner Waterbury Road closes the night from 6:30 to 8 p.m. Leashed dogs are welcome. Please note that this festival was originally planned for September 26, but has been rescheduled due to weather to October 3.. Full program at uptownsoundfest.org. The Montclair Pod is the festival’s official media partner.

Happy Hour & a Half at RecRoom with Toastique Pop-Up

Friday, September 25, 4:30 to 6 p.m. | RecRoom at Lackawanna Station, 1 Lackawanna Plaza

RecRoom kicks off the weekend with its weekly Friday happy hour, this time with a pop-up from Toastique, the Montclair café known for gourmet toast and cold-pressed juices. Toastique’s bottled juices and wellness shots will be available to try and buy.

A Century in Bloom Flower Show at Van Vleck House & Gardens

Friday, September 25, 1 to 5 p.m. | Saturday, September 26, 10 a.m. to 5 p.m. | Sunday, September 27, 11 a.m. to 3 p.m. | Van Vleck House & Gardens, 21 Van Vleck St. | Free

The Garden Club of Montclair marks its 100th anniversary this weekend with a three-day flower show at Van Vleck House & Gardens. Part art gallery, part garden showcase, the show features imaginative floral arrangements, horticulture, photography, flower-inspired art and youth projects, with every exhibit taking inspiration from the past century. The Garden Club has been one of Montclair’s most active civic organizations for a century; this is the event that celebrates all of it.

Fall Fest at the Montclair History Center

Saturday, September 26, 11 a.m. to 4 p.m. | Montclair History Center, 108 Orange Road

The Montclair History Center and Montclair Community Farms team up for their annual Fall Fest on Saturday, a daytime option for families before the music starts uptown. Check the History Center’s site for the full program.

8th Annual Montclair Brewery Oktoberfest

Saturday, September 26, 1 to 10 p.m. | Montclair Brewery, 101 Walnut St. | Tickets required

Montclair Brewery’s Oktoberfest is back for its eighth year, running nine hours with live music from Crow Magnum, Mea and Company, Wake Up Paul and Lil’ Bastad, plus DJ PaP earlier in the day. A local food vendor will be on-site all day. Expect craft beers, hard seltzer cocktails and frozen slushies, plus non-alcoholic options including MB Craft Root Beer, Hop Water and Pineapple Ginger Beer. There’s a costume contest, plus stein-hoisting and keg-lifting competitions throughout the day.

Montclair Dance Festival at the Wellmont Arts Plaza

Sunday, September 27, 10 a.m. to 2 p.m. | Wellmont Arts Plaza, 5 Seymour St. | Free general admission; $25 VIP seating

Freespace Dance’s Montclair Dance Festival returns for its second year, this time at the outdoor Wellmont Arts Plaza, with four hours of free performances from more than 35 dance companies, schools and independent artists from across New Jersey. General admission is free; VIP seating is available for $25.

Also on Saturday and Sunday: the Montclair Flea runs both days at Lackawanna Station, 11 a.m. to 5 p.m., rain or shine, with its usual mix of vintage, handmade goods, art and specialty food. And the Montclair Town-Wide Yard Sale, rained out last weekend, is back this Sunday. Check @montclairyardsale on Instagram for the confirmed map before heading out. (New to it? Here’s how the town-wide sale got started.)

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

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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