If your family spends any time driving Route 302—you’ve probably traveled right past some amazing pieces of history without even realizing it. This Saturday, September 6th, from 10 a.m. to 4 p.m., you’ll have the chance to stop, explore, and experience the past in a whole new way with the first-ever Roosevelt Trail Maine History Tour.

Think of it like a choose-your-own-adventure history trip for families—totally free, self-guided, and designed so you can pop into just one site or make a day of it. Wherever you live in the Sebago Lake Region, chances are you’ll be driving by one of these historic treasures anyway. Why not pull off and step back in time?

What Families Will Love at Each Stop

Here’s a peek at the eight participating locations—and what will get your kids excited to visit:

• Westbrook Historical Society — Explore maps, photos, and artifacts showing how the city transformed from horse-and-buggy days to today.
• Windham Historical Society — A “mini village” with a one-room schoolhouse, meetinghouse, and general store your kids can peek inside.
• Nathaniel Hawthorne’s Boyhood Home (Raymond) — See where the famous author grew up and imagine life without electricity, let alone Wi-Fi.
• Quaker Ridge Meeting House (Casco) — Sit in pews dating back to 1814 and enjoy sweeping views that families gathered around for centuries.
• Raymond-Casco Historical Society — An outdoor and indoor mix of blacksmith shop, one room schoolhouse, antique cars, barn, and more.
• Naples Historical Society & Museum — Discover how Naples became a beloved summer destination long before ice cream stands and mini golf.
• Rufus Porter Museum of Art & Ingenuity (Bridgton) — Perfect for budding artists and inventors, celebrating creativity and hands-on ingenuity.
• Scribner’s Mill & Homestead (Harrison) — Watch a water-powered sawmill in action and step into an 1840s homestead.

Our Visit to the Raymond-Casco Historical Society

Recently I decided to take my two kids to the Raymond-Casco Historical Society—one of the very stops on this tour. I’ll be honest: when I told them we were going, they weren’t exactly thrilled, but within minutes, they were hooked.

We spent an hour taking in a blacksmith demonstration, browsing the antique car collection, testing out the old desks in the one-room schoolhouse, and wandering through the barn and museum packed with relics of the past. Everywhere they turned, there was something new to discover.

What I loved most was how curious it made them. They kept asking questions—“What’s this? Why did people use it this way?”—and those questions turned into great conversations about how different life once was, right here in the same towns we drive through every week. It reminded me that history doesn’t have to feel far away; it can be fun, hands-on, and incredibly meaningful for kids when they get to experience it up close.

Why Families Should Go

• It’s flexible. You don’t have to do all eight stops—pick just one! You’ll likely pass one anyway on your Saturday errands.
• It’s FREE. Museums and societies are opening their doors, offering tours and refreshments at no cost (though donations are welcome).
• It’s kid-friendly. These sites were chosen because they’re engaging, hands-on, and easy to pop in and out of, even with kids in tow.
• It’s local pride. Kids get to see that history isn’t something in faraway cities—it happened right here, in the towns they ride through every week.

Make It Your Family Adventure

Pack some snacks, buckle the kids in, and turn Saturday into a little road trip. Even just one stop could spark a great family conversation about how different life used to be—and how much has stayed the same.

Whether you’ve got a budding artist, inventor, storyteller, or history buff in the family, the Roosevelt Trail Maine History Tour has something they’ll connect with. And who knows—you might even find a new favorite local landmark to revisit.

👉 Mark your calendar: Saturday, September 6th, 10 a.m. – 4 p.m.
👉 Grab your self-guided tour booklet here