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A view of the Housatonic from Tucker’s Ridge

Housatonic Overlook - Tucker's Ridge
Written by Sean Henri

Tucker’s Ridge offers a diverse landscape, stunning views, and wildlife unlike anywhere else in Connecticut, making it the perfect spot for a hike year round.

When the urge to get out and explore nature takes over, head to the southern Connecticut area to check out the dramatic views, engaging trails, and whimsical wildlife that Tucker’s Ridge has to offer.

This place has everything an outdoor enthusiast could possibly ask for. Explore the ridge in all its glory on a beautiful New England day and you’ll be delighted with the nature all around you. All year round, Tucker’s Ridge is a stop for all Connecticut residents.

Housatonic Overlook - Tucker's Ridge

When You’ll Enjoy it Most

From Spring through winter, there really isn’t a bad time to make the trek. Tucker’s Ridge is a favorite during the spring and fall. In the spring, you’ve got mild weather to enjoy, and in the fall you can take in the beautiful autumn foliage, so that makes perfect sense: They’re beautiful times of year to visit.

Though it may not be ideal to hike the trek when there’s snow on the ground, the winter is also the perfect time to spot bald eagles flying over the water or in the trees, so if you want to see this great American symbol then you just might need to brave the cold weather.

Housatonic Overlook - Tucker's Ridge

The Hike

Tucker’s Ridge, set along the 200-foot palisades of the Housatonic river, offers hikers the chance to hike five different trails all with a variety of scenery to take in on the way up. You won’t need to walk more than a few yards though to see what is so special about this panoramic view.

You may spot a bald eagle nesting area, many deer, different species of trees, streams, and splendid views overlooking the Housatonic that are unlike anything else in Connecticut. (Keep in mind that the trail does become quite steep at spots, and you will need to cross streams and pass through wetlands, which may not be ideal for some people.)

A part of the trail is actually an old, abandoned dirt road known as the “Old Highway.” When you look out to see what you made this trip for you see the end of the Housatonic’s 149-mile excursion from the Berkshires to Long Island Sound. To the north you overlook Derby in the distance, to the south Milford, and directly to the west you face Shelton. The overlook at the top of the trail is by far the most scenic point of Tucker’s Ridge, especially when you‘re lucky enough to see bald eagles soaring high.

If You Want To Go

Tucker’s Ridge is located on High Ridge Road in Orange. The property is open year round for hiking and allows for snowshoeing or cross country skiing during winter months. There is no fee for parking or entry and it is open to the public. Dogs are permitted on leash. You can find a Tucker’s Ridge trail map here.

This article was originally published in 2009, but has been updated for accuracy and style. 

About the author

Sean Henri

Sean is the founder and editor of The Connecticut Weekender, and CEO and Founder of Pepperland Marketing. He’s a lifelong CT resident and frequently blogs about the outdoors, beer, food, family life and small business in CT. Follow him on Twitter at @SeanHenri.

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