Who doesn’t love a good road trip winding down old back roads?! That is our jam! Want to make it even better? Add 65-degree weather, sunshine and a light breeze- perfection! Top it off with a fun hike and end the day with a small picnic. Those are the days we crave and can’t get enough of!
For our birthday trip, we decided to combine Forrest and I’s date since we can’t seem to catch a break with the rain in Virgina. Our only request for this hike was a flat long hike. Where I couldn’t make my ankle any worse and Forrest could leisurely ride along in his larger stroller. That how we landed on Colonial Historic Park. A beautiful stroll around the island. -not as many views as we’d hoped for but then again, we as a crew are just happy and grateful we get to explore somewhere new together.
Colonial Historic Park encompasses more than the island; there’s a triangle of Yorktown, Jamestown and Williamsburg. We chose to just do the longer 5 mile loop around Jamestown Island. Easy and plentiful parking at the historic site which we didn’t do but it is dog friendly! That trail is about 1.5 miles long. It is $15 a person. This trail is designed to be immersive with the rich history of the island and surrounding area. Also, no cars or bicycles are allowed. It is ADA and stroller friendly. No inclines, it is relatively flat like the loop we chose.

We chose to take the complete loop at five miles, but a shorter route is available at three miles. Signage abounds here- you’ll never get lost! Signage also includes little post along the route. Read more here! The only cavate to this trail is that you, as a pedestrian, will be sharing the road with motorist and bicyclist. While most people had common sense about themselves – others did not. The loop is a one way loop and we made sure to move off the trail for motorist. For us, it made sense to get safely out of the way. It did extend our walk, but we were happy to be out! A nice thing about the sign areas were each had a small pull off area. Those reminded us of the lookouts and stops along the Blue Ridge Parkway. While the views weren’t spectacular at these stops, the signs were loaded with history and area information. If you’re a history geek like me, you’ll love this! We loved the breezy shaded loop that snaked around the island. Plenty of animal activity like scurrying squirrels and birds rustling through the pines kept the kiddos interested. It did look rather mundane after a few miles, but the boardwalks broke that up nicely.



Jamestown Island loop was impressive but not in the way where we were wowed by breath taking views. Sometimes those simple peaceful walks where the birds are chirping, a light breeze is blowing, and you are with your loved ones are the best hikes. We would rate this one a solid 3. I loved how ADA friendly it was. Completely paved and no inclines for the boardwalks -all seamlessly flowed well. Our only downside would be the traffic and sharing the road with motorist, especially the ones not paying attention. It wasn’t a bother but rather a concerned doggy mama. Another incredible destination steeped with history, soaring pines, and beautiful memories.




Finishing up our trip, we had a fun picnic. If you’ve never made an “Adult Lunchable” you are missing out! These will always be our go to after a long hike! We love pairing crackers, deli meats and sliced cheese so everyone can have somethin’ they really enjoy. Atticus is our cheese and cracker dude. Forrest eats everything. Laveena really loves strawberries and Magda is here for the cheese! We add in healthy noshes like broccoli with ranch, fresh fruit and something sweet. It is the perfect way to end an amazing day trip!

Cheers to our next adventure!
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