Downtown Westminster is in for a big stretch. In the span of just 14 days, Main Street hosts the two largest city-run spring events on the calendar: the Wine Stroll on Saturday, April 25, followed by the Flower & Jazz Festival on Saturday, May 9.
Two Saturdays, two very different events, both taking over the same downtown footprint and bringing major foot traffic to downtown Westminster.
Saturday, April 25: Wine Stroll
The Wine Stroll runs from 12:00 to 4:00 p.m. along Main Street. It's a ticketed, adult-focused event featuring local Maryland wines, distilleries, and a brewery, with live entertainment on five stages — Locust Lane, Library, Covalent Spirits, 45 West Main Street, and Center Street.
Ticket options:
VIP tickets are $40 each ($38 each for groups of six or more), and include early access from 10:30 a.m. to 12:00 p.m. for a 90-minute sampling session with wineries, breweries, and distilleries.
Gehr Lot Reserved Seating at $30 per ticket is sold out.
General admission is $15 and available only on the day of the festival at the festival gates. General admission includes two beverage tokens for the Domestic Beverage Tents, access to live entertainment, and large yard games. Guests 12 and under are free.
Festival gates are located at John/Bond Street, Locust Lane, Longwell Avenue, and Center Street, each at Main Street. Free parking is available in any Westminster Municipal Parking Lot.
Saturday, May 9: Flower & Jazz Festival
Two weekends later, the same streets transform for the Flower & Jazz Festival, running 10:00 a.m. to 4:00 p.m. on the Saturday before Mother's Day.
Unlike the Wine Stroll, Flower & Jazz is a free, family-friendly event. The city bills it as a downtown street fair, with:
Local nurseries sell plants, flowers, and shrubs
Over 200 craft and retail vendors
Food vendors
Live entertainment on three stages — Library, Stocksdale, and Covalent Spirits
The Stocksdale Stage leans heavily into the "jazz" half of the festival's name, with sets from the Westminster High School Jazz Ensemble, Sunday Night Big Band, Market Street Big Band, Swingin' Harmony Big Band, the McDaniel College Jazz Ensemble, and the Carroll Community College Rock Ensemble filling the day.
A Safe Kids Zone, presented by the Carroll County Health Department, will operate in the Gehr Lot with programming on bicycle safety, 911, emergency preparedness, poison prevention, and children's mental health. And in a Mother's Day weekend touch, moms can stop by the City of Westminster tent for a free flower.
Free parking is available in all City municipal lots, with organizers recommending the Westminster Square Garage behind the city offices, the Sherwood Parking Lot behind the Westminster Exchange Building, and the Longwell Parking Garage.
Main Street, Back to Back
Between them, the two festivals span the back half of April and the start of May, a two-week window that has quietly become one of the busiest stretches on Westminster's downtown calendar. For Main Street businesses, it's an early-season boost; for residents, it's two very different reasons to come downtown on a Saturday.