The Pomperaug Trail follows the Pomperaug River which has been dammed in some places so it feels more like a lake.
The deep blue water peaks through the trees at several overlooks. The ground is padded with cushy dirt and moss. Follow the trail past three cascading waterfalls.
Get Ready: Pomperaug Trail is in Oxford, Connecticut, directly north of Bridgeport. If you’re coming from the Stamford area you’ll take I-95 to CT8 N. If you’re coming from the east, jump on CT8 S. You’re going to park at what seems like an odd location, back in a neighborhood in an unpaved circle drive at the end of Fiddlehead Road.
Get set: If you’re looking towards the dead end, the trail will be up and to your right. Get to it.
Go: It’s a 3.7 mile trail that will bring you up 850 feet of elevation. This trail isn’t for the faint of heart. The beginning of your journey will take you along the Zoar River. It’s quite beautiful and peaceful. You’ll make your way through the trees on your right and the view on your left. You’ll pass by three waterfalls. You might get your feet wet. This is where the trail loops around to your right and back to where you came from. If you’ve gone too far you’ll enter a clearing that is Jackson Cove Park. There’s an opportunity to swim or play on the playground – if you want your hike to be a little longer, you can just keep trekkin’ through the park. The Pomperaug Trail picks back up in a few hundred feet but enters onto private land.
Takeaway: There’s quite a bit of up and down. Some people might prefer to hike this trail with trekking poles. The loop around could be easy to miss, so keep your eyes peeled. I’ll definitely be back here again!