Mother pushing her baby in a stroller during the fall

Every now and then, you just need to grab the stroller, bundle up the kids, and step outside for fresh air. That’s why we’ve compiled a list of five stroller-friendly walks (or runs if you wish!) in Plymouth that are on our to-do list this month.

Mom reading a page from a book on a walk with her two children.

Plymouth Family Network Story Walk

Forges Field, Jordan Road | November 7 – December 31

Discover Plymouth Family Network’s new story walk at Forges Field with “It’s Okay to be Different” by Todd Parr, starting November 7. The story walk adventure begins at the baseball field parking lot and ends near the pavilion. For longer strolls, explore the paved walkways around Forges Field. Or, if the little ones need a break, there’s a playground at the story walk’s end to let them burn off some energy. Enjoy the story and a great walk!


View of the portico over Plymouth Rock with water in the background.

Downtown Plymouth

Free and paid lots available along Water Street

Explore Plymouth’s waterfront year-round! Start by parking in one of the lots on Water Street. Follow the scenic walking path from there to Plymouth Grist Mill and take in the sights, including Plymouth Rock, the Mayflower II, Brewster Gardens, and of course, Plymouth Grist Mill itself. Be sure to grab a delicious meal at one of the fantastic restaurants or enjoy some shopping at small businesses along the way.


Nelson Beach Park
See Plymouth

North Plymouth Rail Trail / Grace Trail ®

Nelson Memorial Park, 255 Water Street

Savor scenic views with a walk along part of the historic Old Colony Railroad, spanning just over a mile. It’s also home to the original Grace Trail®, offering a serene opportunity for self-reflection. Begin and end your journey at Nelson Memorial Park, and don’t forget to treat the kids to some fun at the playground afterward.


Running of the Pilgrims 5k logo with a turkey chasing a Pilgrim
South Shore Race Management

7th Annual Running of the Pilgrims

Plymouth Rock, Water Street | November 23, 2023 at 7:30 AM

While other towns have Turkey Trots, America’s Hometown offers its own twist – the annual Running of the Pilgrims! You can walk or run this stroller-friendly 5k, starting at historic Plymouth Rock at 7:30 AM on Thanksgiving morning. Registration is $30 for adults, $20 for children 5-10, and free for children 5 and under through November 21. Don’t miss this Plymouth tradition!


Winter Lights 5k Logo. A Christmas tree with lights.
South Shore Race Management

12th Annual Winter Lights 5k

Intersection of Court Street and Howland Street | December 1, 2023 at 6:15 PM

Kickstart your holiday season with the Winter Lights 5k! As part of the Christmas in Historic Plymouth event, you can meet Santa, savor hot chocolate, and enjoy a stroller-friendly 5k once the tree is lit. Registration is $35 for adults, $25 for children 5-10, and free for children 5 and under. Plus, get a $10 discount when you combine the Running of the Pilgrims and Winter Lights 5k. Enjoy a festive double-header that’s sure to light up your holiday spirit!


Mom pushing a stroller with toddler walking beside it during the fall

From picturesque waterfront trails to traditional 5ks, these walks promise not only beautiful scenery but also the chance to make cherished family memories. Let’s lace up those sneakers and hit the trails! This Cape Cod Mom hopes to see you out there.


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