Gay Street Open Air Market 2026
Downtown West Chester N. High and Gay Street, West Chester, PAThe Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Discover the best family-friendly things to do in and around the Main Line with kids, including events, festivals, attractions, and free activities through our curated calendar. Find what’s happening in Chester, Delaware, and Montgomery Counties today and plan your next family adventure!
💞 Check out our sister Community Calendars too: Philadelphia Family and Bucks County Parent.
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The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Enjoy Baby Whale and the Plastic Ocean during the 2026 Philadelphia Fringe Festival!
King of Prussia will host the incredible Montco Jazz Fest as it marks its 5th Anniversary. Held on Eataly's terrace on September 11th & 18th, music lovers and jazz fans are welcomed for a six day celebration of extraordinary music, unforgettable performances, and a celebration of the rich legacy of jazz throughout Montgomery County, Pennsylvania.
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Colonial history will come to life in Tredyffrin Township this September when His Majesty’s 40th Regiment, 2nd Battalion Light Infantry – the “Bloodhounds” – establishes an authentic Revolutionary War encampment at Teegarden Park in Tredyffrin Township as part of Chester County’s 250th anniversary celebration.
Kick off the fall semester with an afternoon of fun, flavor, and community at Creutzburg! The community is invited to join Main Line School Night on Saturday, September 19, from 12:00–4:00 pm for an afternoon filled with tasty bites, local artisans, live music, games, dance, and hands-on demonstrations from MLSN instructors. Whether attendees are 9 or 90, there will be something for every lifelong learner!
The Borough of Conshohocken invites you to the 33rd Annual Funfest on Saturday, September 19, from noon to 8 p.m., taking over Fayette Street for a celebration bigger and better than ever before.
Enjoy Baby Whale and the Plastic Ocean during the 2026 Philadelphia Fringe Festival!
The HEADstrong Foundation is bringing its Running aHEAD of Cancer 5K back to Swarthmore this fall. Runners, walkers, and supporters are invited to come together for a 5K run and 1-mile walk. Kids and strollers are welcome, making the event open to the whole family. The event supports HEADstrong’s mission and Nick’s House, which provides free accommodations and support to families traveling for cancer treatment.
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Colonial history will come to life in Tredyffrin Township this September when His Majesty’s 40th Regiment, 2nd Battalion Light Infantry – the “Bloodhounds” – establishes an authentic Revolutionary War encampment at Teegarden Park in Tredyffrin Township as part of Chester County’s 250th anniversary celebration.
Join Le Mignon for a 90-minute hands-on Mooncake Baking Class on Sunday, September 13th and Sunday, September 20th.
As summer draws to a close, families are invited to the Circle Garden for a family-friendly concert celebrating the beginning of autumn with Miss Virginia and her supergroup of area children’s musicians, Miss Laura and Mr. Anthony.
Enjoy Baby Whale and the Plastic Ocean during the 2026 Philadelphia Fringe Festival!
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Renew You's West Chester Open House is approaching. Step into their new space, meet team members, and get a feel for the many ways reNEW YOU supports mental health and whole-person wellness.
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Explore Sacred Heart Academy at its open house and fun fair event on September 26th. Enjoy Explore the spirit through interactive tours, performances, and family fun!
Sacred Heart Academy comes together for a day of community, connection, and fun at its Open House and Family Fun Fair.
Step up to the flower bar and create your own bouquet using locally grown, seasonal blooms from area farms. Bring a vase or container from home (or choose from our stash of recycled ones) and design something beautiful while supporting sustainable flowers and local growers.
Canine Partners for Life (CPL), a non-profit organization located in Chester County, PA, is dedicated to increasing the independence and quality of life of individuals with physical, developmental, and cognitive disabilities or who are in other situations of need, by training and placing service and companion dogs.
Uptown! Knauer Performing Arts Center is thrilled to bring back its free pop-up Beer Garden series—an open-air celebration of community, live music, and fun.
Get tickets now for the spectacular Fireworks & Fountains Shows at Longwood Gardens. Experience everything from a Journey to Oz that defies gravity to a swoon-worthy show of classics, to the magic of Leroy Anderson, space-themed hits, 80s tunes, and more.
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Gather your family, friends, and colleagues for an exciting Topgolf event benefiting Take A Breather Foundation. Your participation helps fund life-changing respite experiences that allow individuals and families living with cystic fibrosis to take a break from treatments and focus on making memories together.
The Wit You Against Childhood Cancer fundraising rally is a family-focused, community event hosted annually at Philadelphia’s Smith Memorial Playground.
Boo at the Zoo returns on weekends from October 3 through November 1, transforming the Zoo into a kooky, spooky celebration for the whole family.
Get ready for a frighteningly good time! Mark your calendars for Saturday, October 3rd from 3 PM to 8 PM (rain date: Sunday October 4th) for Shiverfest, Riverbend's largest family fall festival. Expect a trick or treat trail, an insect show, face painting, pony rides, haunted trails, arts and crafts, food trucks, and more!
Boo at the Zoo returns on weekends from October 3 through November 1, transforming the Zoo into a kooky, spooky celebration for the whole family.
A FREE introduction to symphonic music for elementary and middle school age students accompanied by a parent or guardian. Sponsored by Delaware County Symphony.
Boo at the Zoo returns on weekends from October 3 through November 1, transforming the Zoo into a kooky, spooky celebration for the whole family.
Join former Chester County Trails Club Vice President Dolores (Dee) McGrath for a three-mile hike through a historic area, ending with 10 minutes of quietly enjoying the sounds of nature.
Boo at the Zoo returns on weekends from October 3 through November 1, transforming the Zoo into a kooky, spooky celebration for the whole family.
The annual festival at St. Mary's Episcopal Church on the corner of Lancaster and Louella Avenues welcomes the Wayne community and beyond!