The May Events You Won’t Want to Miss Around the Main Line

Look out for a self-guided art tour in West Chester, a craft fair in Exton, the Devon Horse Show and more around the Main Line this May.

Main Line Today recommendations are objective, unbiased, and curated by the editorial team. If you buy something through our links, we may earn an affiliate commission at no cost to you.

Check out our calendar for more events throughout May.

Editor’s Pick

May 18-19

Derby at the Vineyard

Chadds Ford

This unique weekend event is being billed as a “celebration of the good life” by its hosts, Penns Woods Winery and Paradox Country Farm. Sip a glass of wine and look on as skilled riders navigate challenging courses atop their horses. Both days also feature live music and an artisan market—and little ones can meet the horses and their riders. Visit —G.L.

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May Spring Gallery Walk
Courtesy West Chester BID

May 3

Spring Gallery Walk

West Chester

Local artists display their work throughout this self-guided art tour of downtown West Chester. Pop into local businesses and galleries to meet fellow creatives—and maybe even fall in love with a piece for your home. Refreshments and light appetizers are also part of the evening. Visit

May 4

Spring Craft Fair


Searching for the perfect Mother’s Day gift? There’s a good chance you’ll find what you’re looking for at this seasonal extravaganza featuring some 70 vendors. We won’t blame you for picking up something special for yourself, too. Visit

Festival of Fountains
Courtesy of Longwood Gardens

May 9–Sept. 29

Festival of Fountains

Kennett Square

The 1,719 jets that make Longwood Gardens’ fountains so spectacular are artfully choreographed to a rousing soundtrack. The stunning combination of brilliant landscape design and innovative technology never gets old. Shows take place throughout the day. Visit

May 17-31

Festival of the Peony

Chadds Ford

Fields of fragrant peonies are in their full glory at this annual festival. Choose to walk or drive amid the blooms, and be sure to purchase your own cut flowers at the gate. Visit

Clover Market May
Courtesy of Clover Market

May 19

Clover Market

Bryn Mawr

Clover Market has fast become a cherished annual tradition in Bryn Mawr. Expect over 90 vendors offering handmade and vintage goods, along with food trucks, live music and free kids’ crafts. Visit

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Devon Horse Show
Photo by Brenda Carpenter

May 22–June 2

Devon Horse Show


This renowned Main Line institution is in its 128th year, and extensive improvements have been made to better accommodate both riders and spectators. Horse enthusiasts won’t be disappointed, with skilled equestrians competing for almost $1 million in prize money. The diverse lineup of family-friendly fun spans over 12 days. This year’s Ladies Day is May 29. Proceeds benefit Bryn Mawr Hospital. Visit

What We’re Reading

Inspired by a family vacation to Lake George, New York, Gilbertsville author and paranormal investigator

Mallory Cywinski shares this spooky slice of suspenseful fiction tempered by a touch of romance. Desperate Creatures follows Mara Cooke, a successful young author who suffers a life-altering accident one summer evening. In a desperate attempt to reclaim her life and escape the endless guilt weighing her down, she flees to a lakeside cabin in the Adirondack Mountains, where things take a creepy paranormal turn. Brace yourself for an ending you won’t see coming. $14.99, 265 pages. Available through Amazon.

Desperate Creatures book
Courtesy of Mallory Cywinski

Related: Here’s What to Do Around the Main Line Area This Weekend

Our Best of the Main Line Elimination Ballot is open through February 22!