5 Winter Hikes for Families in Greater New Haven

By By Makayla Silva, Macaroni Kid New Haven - Milford Editor & Publisherl January 9, 2021

Winter is a wonderful time of year to hike. Blankets of snow and the crisp, cold air bring a fresh perspective to many of our favorite, familiar places. Views are clearer and unobstructed, bugs are a non-issue, and animal tracks turn us all into snow detectives. Check out some of our favorite local spots for winter hiking. 

Pile on the layers and get out there already! Tip: Pack a thermos with warm tea or cocoa!

1. Racebrook Tract - Woodbridge
Spanning 230 acres of meandering trails, the Racebrook Tract is a marvelous green space teeming with wildlife, songbirds and streams. This is my family's favorite local spot to explore, visiting it each and every week.  Racebrook is a wonderful place to birdwatch and test out your winter "pishing" skills. Don'tforget the binoculars!

2. Common Ground - New Haven 
Starting from Common Ground High School, The Old Oak Nature Trail Loop is about 30 minutes of flat and uphill hiking to get to Judge’s Cave and one for even the younger set. Trails are NOT stroller accessible. Once you reach the top, your kiddos will want to spend some time exploring the cave before making the 30 minute climb back down. (We suggest packing a picnic to enjoy at the top of the summit!) 

3. Eisenhower Park – Milford 
Tucked down the hill from the widely popular Bodie’s Place playground, Eisenhower Park is a hidden gem in New Haven County. With mostly-flat terrain to traverse, Eisenhower Park offers easy, kid-friendly trails perfect for the youngest hiker. My kids love to travel along the StoryWalk and read the pages of the storybook along the trail. 

4. Housatonic Overlook and Tucker's Ridge - Orange
Park your car at the end of the aptly named High Ridge Road, walk about 20 steps for a super kid-friendly hike with some pretty amazing views. Tucker's Ridge overlooks the Housatonic River, boasts a seasonal waterfall and features a letterbox! If you're lucky, you might spot bald eagles flying over the water or in the trees.

5. Giant Steps Trail - New Haven
Okay so this hike is certainly not as easy because it is actually quite steep. But it is only a quarter of a mile and the view of New Haven is worth the climb. Once at the top, your kiddos will love to run around in the large open field.

Take our Winter Scavenger Hunt along with you on your hike and Tag #MacKidNewHaven to be Featured!