The Best Things To Do Around the Main Line with Kids

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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Main Line Parent Community Calendar

  • Babble and Books at Harmony Kids Playhouse

    Babble and Books at Harmony Kids Playhouse

    Harmony Kids Playhouse 7 West Baltimore Ave., Media, PA

    Join Harmony Kids Playhouse for a story time and play session designed to boost your child’s early language skills! Led by Ms. Tina, a Speech and Language Pathologist (SLP) from The Speech & Language Center, Babble & Books combines 30 minutes of interactive story time with 30 minutes of open […]

  • The Philadelphia Ballet presents The Nutcracker

    Academy of Music 240 S Broad St, Philadelphia, PA, United States

    Treat your family to the memorable experience of George Balanchine’s The Nutcracker®, a must-see holiday classic! The holiday season comes to the stage in the Philadelphia Ballet's annual performance, a tradition unlike any other. Cross swords with the Mouse King and dine with the Sugarplum Fairy in this quintessential celebration […]

  • The Trail to Oregon at Wolf Performing Arts Center

    Wolf Performing Arts Center 1240 Montrose Avenue, Bryn Mawr, PA

    The Trail to Oregon! follows a hilariously inept American family as they embark on a perilous 1800s journey from Missouri to Oregon. This musical parody of the classic Oregon Trail video game delivers non-stop laughs through memorable songs and absurd humor. Expect a riotous adventure that turns the challenges of […]

  • Annie at the Media Theatre

    Annie at the Media Theatre

    The Media Theatre 104 E. State Street, Media, PA, United States

    The Media Theatre's Broadway Series brings the story of orphan Annie to their Delco stage this winter. Sing along with the classic songs you've grown to know and love this holiday season. Immerse yourself in a world of impressive dancing and acting as this feel-good story is brought to life.

  • A Christmas Story the Musical

    A Christmas Story the Musical

    Walnut Street Theatre 825 Walnut St, Philadelphia, PA, United States

    Experience the charm and humor of A Christmas Story The Musical at the Walnut Street Theatre this holiday season. Join Ralphie and his family and experience their hilarious antics. Although he only has one holiday wish to get a Red Rider BB gun on Christmas morning, Ralphie finds himself foiled […]

  • Lights Up! Holiday Weekends in West Chester

    Lights Up! Holiday Weekends in West Chester

    The Greater West Chester Chamber of Commerce 137 N High Street, West Chester, PA, United States

    Voted one of USA Today’s Top Places to See Santa Claus, more than 80,000 lights glow in West Chester this holiday season during Lights Up Holiday Weekends in West Chester. Enjoy free family fun including free photos with Santa in front of M&T Bank on the Square with their new […]

    Free
  • A Longwood Christmas

    A Longwood Christmas

    Longwood Gardens 1001 Longwood Road, Kennett Square, PA

    Step into a world of glittering jewels and timeless elegance this holiday season as A Longwood Christmas returns November 21, 2025, through January 11, 2026. This Christmas, Longwood's Gardens are transformed into a living jewel box as radiant as the jewels and gems that inspired it. Longwood’s grand conservatories come alive […]

  • A Christmas Carol at Walnut Street Theatre

    A Christmas Carol at Walnut Street Theatre

    Walnut Street Theatre 825 Walnut St, Philadelphia, PA, United States

    This holiday season, the Walnut Street Theatre for Kids presents a special hour-long musical adaptation of Charles Dickens' A CHRISTMAS CAROL perfect for kids and families. Using traditional songs to re-tell Dickens’ fantastical story, come along as Ebenezer Scrooge is visited by three ghosts who show him the past, present, […]

  • A Christmas Story the Musical

    A Christmas Story the Musical

    Walnut Street Theatre 825 Walnut St, Philadelphia, PA, United States

    Experience the charm and humor of A Christmas Story The Musical at the Walnut Street Theatre this holiday season. Join Ralphie and his family and experience their hilarious antics. Although he only has one holiday wish to get a Red Rider BB gun on Christmas morning, Ralphie finds himself foiled […]

  • Rudolph The Red Nosed Reindeer The Musical Jr.

    Rudolph The Red Nosed Reindeer The Musical Jr.

    The Springer Studio Youth Theater 751 Pike Springs Road, Phoenixville, PA

    Catch the musical production of Rudolph The Red Nosed Reindeer The Musical Jr. this holiday season. Learn of the humble beginnings of the red-nosed holiday hero everyone knows and loves. With an upbeat musical score and lovable characters, this show features children in grades 4 through 8. The Springer Studio […]

  • The Philadelphia Ballet presents The Nutcracker

    Academy of Music 240 S Broad St, Philadelphia, PA, United States

    Treat your family to the memorable experience of George Balanchine’s The Nutcracker®, a must-see holiday classic! The holiday season comes to the stage in the Philadelphia Ballet's annual performance, a tradition unlike any other. Cross swords with the Mouse King and dine with the Sugarplum Fairy in this quintessential celebration […]

  • The Trail to Oregon at Wolf Performing Arts Center

    Wolf Performing Arts Center 1240 Montrose Avenue, Bryn Mawr, PA

    The Trail to Oregon! follows a hilariously inept American family as they embark on a perilous 1800s journey from Missouri to Oregon. This musical parody of the classic Oregon Trail video game delivers non-stop laughs through memorable songs and absurd humor. Expect a riotous adventure that turns the challenges of […]

  • Annie at the Media Theatre

    Annie at the Media Theatre

    The Media Theatre 104 E. State Street, Media, PA, United States

    The Media Theatre's Broadway Series brings the story of orphan Annie to their Delco stage this winter. Sing along with the classic songs you've grown to know and love this holiday season. Immerse yourself in a world of impressive dancing and acting as this feel-good story is brought to life.

  • Evil Dead The Musical in Berwyn

    Evil Dead The Musical in Berwyn

    Footlighters Theater 58 Main Avenue, Berwyn, PA, United States

    Footlighters Theater is a non-profit theater that has provided quality, affordable family and adult entertainment to the Main Line for over 90 years. This holiday season, the theater is featuring Evil Dead The Musical, a show that turns concepts from a duo of horror films into a comedic musical. In […]

  • Kimberton Waldorf School: Waldorf 101 Parent Support Series

    Kimberton Waldorf School 410 W. Seven Stars Road, Phoenixville, PA, United States

    Kimberton Waldorf School will be offering a Waldorf 101 Parent Support Series for the 2025–26 school year! Come to the school on select Saturday mornings from 9:00 to 10:30 am, where a variety of experienced speakers will share insights into Waldorf education and the journey of parenting children of all […]

  • Lights Up! Holiday Weekends in West Chester

    Lights Up! Holiday Weekends in West Chester

    The Greater West Chester Chamber of Commerce 137 N High Street, West Chester, PA, United States

    Voted one of USA Today’s Top Places to See Santa Claus, more than 80,000 lights glow in West Chester this holiday season during Lights Up Holiday Weekends in West Chester. Enjoy free family fun including free photos with Santa in front of M&T Bank on the Square with their new […]

    Free
  • A Longwood Christmas

    A Longwood Christmas

    Longwood Gardens 1001 Longwood Road, Kennett Square, PA

    Step into a world of glittering jewels and timeless elegance this holiday season as A Longwood Christmas returns November 21, 2025, through January 11, 2026. This Christmas, Longwood's Gardens are transformed into a living jewel box as radiant as the jewels and gems that inspired it. Longwood’s grand conservatories come alive […]

  • Shrek the Musical KIDS!

    Shrek the Musical KIDS!

    Hedgerow Theatre 64 Rose Valley Road, Media, PA

    The Hedgerow Theatre School students bring everyone's favorite green ogre to the stage with their performance of Shrek the Musical KIDS. Laugh along the way as Shrek, Donkey, and a cadre of eccentric fairytale friends attempt to save Princess Fiona and reclaim Shrek's swamp home from Lord Farquaad. These performances […]

  • A Christmas Carol at Walnut Street Theatre

    A Christmas Carol at Walnut Street Theatre

    Walnut Street Theatre 825 Walnut St, Philadelphia, PA, United States

    This holiday season, the Walnut Street Theatre for Kids presents a special hour-long musical adaptation of Charles Dickens' A CHRISTMAS CAROL perfect for kids and families. Using traditional songs to re-tell Dickens’ fantastical story, come along as Ebenezer Scrooge is visited by three ghosts who show him the past, present, […]

  • The Tapcracker

    The Tapcracker

    Suzanne Roberts Theater 480 S Broad Street, Philadelphia, PA, United States

    This holiday season, join The Lady Hoofers Tap Ensemble, Philadelphia’s own all-women tap company, for The Tapcracker! With a cast of over 40 dancers from PA, NJ, and DE, The Tapcracker transports audiences to Paris, where an infestation of rats has thrown the city into chaos. Toy soldiers guard the […]

    $35 – $65
  • Kennett Square Holiday Village Market

    Kennett Square Holiday Village Market

    The Creamery of Kennett Square 401 Birch Street, Kennett Square, PA, United States

    The Kennett Square Holiday Village Market, modeled on the German Christkindlmarkt, features dozens of curated artisan and vintage vendors as well as live music, ice sculptures, food trucks, Santa Claus, and more in the magical setting of The Creamery. The Holiday Village Market is a curated shopping and dining experience in […]

  • 6th Annual West Chester Christkindlmarkt

    Downtown West Chester N. High and Gay Street, West Chester, PA

    Experience the magic of the holiday season at the Chriskindlmarkt on Gay Street in downtown West Chester, hosted by the Chester County Art Association! This outdoor market is a holiday tradition, where you can shop unique, handcrafted gifts from local artisans, enjoy seasonal treats, and celebrate with live music and […]

  • Rudolph The Red Nosed Reindeer The Musical Jr.

    Rudolph The Red Nosed Reindeer The Musical Jr.

    The Springer Studio Youth Theater 751 Pike Springs Road, Phoenixville, PA

    Catch the musical production of Rudolph The Red Nosed Reindeer The Musical Jr. this holiday season. Learn of the humble beginnings of the red-nosed holiday hero everyone knows and loves. With an upbeat musical score and lovable characters, this show features children in grades 4 through 8. The Springer Studio […]

  • Habitat Stewards at Newlin Grist Mill

    Habitat Stewards at Newlin Grist Mill

    Newlin Grist Mill 219 Cheyney Road, Glen Mills, PA

    Help make the park a better place for wildlife and people! The Habitat Stewards group meets once a month to work on outdoor tasks related to habitat restoration and species conservation. Projects vary by month but include things like invasive plant removal, tree planting, garden maintenance, trail cleanup, and outdoor […]

    Free
  • The Nutcracker | 25th Anniversary

    The Nutcracker at the Grand Opera House, Wilmington

    grand opera house 818 N Market Street, Wilmington, DE, United States

    Experience Delaware’s Holiday Tradition at The Grand Opera House with First State Ballet. Celebrate the season with Delaware’s professional ballet company! Share in Marie’s holiday dream and experience a magical journey through a swirling snowstorm to the Land of Sweets in this lavish production.

  • A Christmas Story the Musical

    A Christmas Story the Musical

    Walnut Street Theatre 825 Walnut St, Philadelphia, PA, United States

    Experience the charm and humor of A Christmas Story The Musical at the Walnut Street Theatre this holiday season. Join Ralphie and his family and experience their hilarious antics. Although he only has one holiday wish to get a Red Rider BB gun on Christmas morning, Ralphie finds himself foiled […]

  • The Trail to Oregon at Wolf Performing Arts Center

    Wolf Performing Arts Center 1240 Montrose Avenue, Bryn Mawr, PA

    The Trail to Oregon! follows a hilariously inept American family as they embark on a perilous 1800s journey from Missouri to Oregon. This musical parody of the classic Oregon Trail video game delivers non-stop laughs through memorable songs and absurd humor. Expect a riotous adventure that turns the challenges of […]

  • Philly Pops: A Philly Holiday Spectacular

    Philly Pops: A Philly Holiday Spectacular

    Marian Anderson Hall, Kimmel Center 300 S Broad St, Philadelphia, PA 19102, Philadelphia, PA, United States

    Get your holiday started on a festive footing as the Philly Pops present A Philly Holiday Spectacular. Conducted by new Musical Director, Chris Dragon, this show will be filled with holiday favorites and special guests including The Philadelphia Boys' Choir, the St. Thomas Gospel Choir, the Philly Pops Chorus, and […]

  • Downingtown Good Neighbor Christmas Parade

    Beaver Creek Elementary School 601 W. Pennsylvania Ave., Downingtown, PA

    Join friends and neighbors for Downingtown's hometown Christmas parade featuring local bands, floats, businesses, scouts, dance troupes, and Santa! The parade follows a 1.7 mile route along Lancaster Avenue through the heart of Downingtown. The parade starts at Gable Ave., turning left on Lancaster Ave. and proceeding to the finish […]

  • The Nutcracker | 25th Anniversary

    The Nutcracker at the Grand Opera House, Wilmington

    grand opera house 818 N Market Street, Wilmington, DE, United States

    Experience Delaware’s Holiday Tradition at The Grand Opera House with First State Ballet. Celebrate the season with Delaware’s professional ballet company! Share in Marie’s holiday dream and experience a magical journey through a swirling snowstorm to the Land of Sweets in this lavish production.

  • A Christmas Carol at People’s Light

    A Christmas Carol at People’s Light

    People's Light 39 Conestoga Road, Malvern, PA, United States

    Join People's Light for their creative re-telling of the Charles Dickens classic, A Christmas Carol. Featuring both original songs and traditional English carols, this performance sets the stage for a memorable holiday season with its exploration of themes including family and forgiveness. Plan an outing the whole family will enjoy […]

  • Annie at the Media Theatre

    Annie at the Media Theatre

    The Media Theatre 104 E. State Street, Media, PA, United States

    The Media Theatre's Broadway Series brings the story of orphan Annie to their Delco stage this winter. Sing along with the classic songs you've grown to know and love this holiday season. Immerse yourself in a world of impressive dancing and acting as this feel-good story is brought to life.

  • Evil Dead The Musical in Berwyn

    Evil Dead The Musical in Berwyn

    Footlighters Theater 58 Main Avenue, Berwyn, PA, United States

    Footlighters Theater is a non-profit theater that has provided quality, affordable family and adult entertainment to the Main Line for over 90 years. This holiday season, the theater is featuring Evil Dead The Musical, a show that turns concepts from a duo of horror films into a comedic musical. In […]