Large long hiking trail and Lake Mohegan surrounded by tall green trees shading the trail

CT/NY Hiking Recommendations for May 2022

April can be a bit wet (those April showers), but in May things start to dry up a bit. So, while those April showers may have kept you off the trails, the May flowers will have you itching to get outdoors again. If you’re wondering where to hike near Connecticut or New York in May 2022, then I have 4 hiking recommendations for you! 

For May 2022 I am recommending the following parks/trails: 

West Rock Ridge State Park (West Haven/Hamden, CT) 

Rye Marshlands Conservancy (Rye, NY) 

Lake Mohegan (Fairfield, CT) 

Trout Brook Valley (Easton, CT)

These encompass a variety of easy-to-medium trails that are great for the entire family (including the pups) to enjoy. 

small dirt path winding around Lake Mohegan in Fairfield

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West Rock Ridge State Park: West Haven, Hamden, and Woodbridge, CT

West Rock Ridge State Park is a pretty expansive park. But, because of that there are a lot of different trails and experiences to try. Plus, it’s proximity to New Haven allow you to hike in the day, followed by a dinner or desert (ice cream, anyone?) after a long day on the trails. 

Depending on the trail you choose, there are some pretty beautiful view points of Hamden/Woodbrige. But, if you aren’t really into elevation climbs, there are large ponds to stroll around and enjoy. If you’re into kayaking, these can be kayaked as well (but you’ll need to bring your own yak).

Before heading to this park, check out my guide to the Regicides trail. It is a medium-level trail that contains both views and flat strolls. 

Overlooking Lake Dawson in Hamden Connecticut from the blue regicides trail at West Rock Ridge State Park

Rye Marshlands Conservancy: Rye, NY

Rye Marshlands Conservancy is probably the most family friendly hike I’ve done in the area. Not only are the trails easy, and the landscape stunning, but there is TONS of wildlife to see.

If you or your child enjoy spotting animals around you, then this will be the park for you. Part of the trail allows you to hike down into the Marsh, which can be muddy (so be prepared for mud). But the view from inside the marsh is incredible and a unique experience that is completely worth the visit. 

If you want to explore this park but aren’t sure where to start, check out my guide to hiking Rye Marshlands Conservancy, which will list a parking lot, trail, and everything else you should know to hike here for the first time. 

rye marshlands conservatory views

Lake Mohegan: Fairfield, CT

Lake Mohegan is a VERY popular park. This is primarily because it has a swimming area for residents, but also because it’s one of the only off-leash dog hiking trails in the area. 

If you LOVE pups, then this trail is absolutely for you. Expect several off-leash dogs running around and jumping in to swim at the lake. It’s a great way to meet other dog owners, and to let your pup get some exercise. 

If dogs really aren’t your thing – no worries, this is still a fantastic hike. After you get past the first dog swimming hole, the crowd gets MUCH smaller, and it seems almost remote as you head to the backside of the lake. 

Back here there are picnic tables and grills to use and is much less crowded than the front of the park. 

Check out my guide to hiking Lake Mohegan here.

Large long hiking trail and Lake Mohegan surrounded by tall green trees shading the trail

Trout Brook Valley: Weston, CT

If you’re looking for a remote, secluded, and quiet area then Trout Brook Valley is for you. There likely will be other hikers, but it is so easy to spread out and you may not even see anyone else except in passing. 

The cell service isn’t great though, so make sure you’ve downloaded a trail or packed a map before heading gout. 

This remote area is popular for trail runners, more secluded hiking, and has areas for equestrian use. One trail even allows for off-leash dogs. So, you really do get a bit of everything here. 

If you’re looking to hike at Trout Brook Valley this May, check out my complete guide here. 

Trail Bridge at Trout Brook Valley

I hope you’ve found a hike in our CT/NY Hiking Recommendations for May 2022 that you’ll be hiking this month. Remember to check in with us again for June’s recommendations, or subscribe below to receive our monthly recommendations directly to your inbox! 

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