Where Can I Hike Near New Haven, CT: 9 Amazing Trails for Everyone

If you ask people from New Haven where to hike – you’ll get several great park recommendations. Sleeping Giant, West Rock Ridge, or even East Rock Park offer great ways to get into nature without traveling too far away. But what you often don’t learn is which hiking trails are the best trails around New Haven, Connecticut. 

These bigger parks have so many trails it can be hard to determine which one to do, especially if you’re looking only for a certain level of hike (easy, medium, or hard). Around New Haven, Lake Wintergreen, Racebrook, and Peter’s Rock are fantastic easy hikes,  while, Regicides, East Rock Loop, and the Yellow/Orange trails at Sleeping Giant are perfect for medium level hikers. For those looking for harder trails, check out the Blue Trail at Sleeping Giant or the NET for more of a challenge. 

Let’s look into the each of these hiking trails around New Haven, CT in more detail, so you can choose the best trail for you!  

Summary of the Best Hiking Trails around New Haven, CT

Rating	Trail Name	Park	Distance	Elevation
Easy	Lake Wintergreen Trail	West Rock Ridge	1.5 miles	55 ft.
Easy	Racebrook, Pine, Wepawaug Trail	Orange, CT (41.30305N, 73.01763W)	2.8 miles	134 ft.
Easy	Peter’s Rock Circuit	Peter’s Rock Park	3.6 miles	583 ft.
Medium	East Rock Loop	East Rock Park	2.2 miles	383 ft.
Medium	Yellow/Orange Loop	Sleeping Giant State Park	4.5 miles	846 ft.
Medium	Regicides Trail	West Rock Ridge	6.9 miles	921 ft.
Medium	White Trail	Sleeping Giant State Park	5.4 miles	1535 ft.
Hard	Blue/Violet Loop	Sleeping Giant State Park	8.0 miles	1692 ft.
Hard	New England Trail	Guildford, CT	207.3 miles (to complete)	31,482 ft. (to complete)

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Easy Hiking Trails Around New Haven: Location and Details

The three easy hiking trails around New Haven, CT that I am highlighting here are perfect trails for beginners. Not only are they fairly easy to complete, but they also have beautiful nature views that may just keep you finding new trails to explore: 

Lake Wintergreen Trail in West Rock Ridge State Park (Hamden, CT) is the shortest, and likely easiest of the three easy trails I’m highlighting here. The trail starts here and goes around the entirety of Lake Wintergreen. It’s a great trail for dogs, and children, as it’s mostly flat and even has some paved portions. You can find a complete map of the trail here. 

Racebrook, Pine, and Wepaqaug Trails in Orange, CT (Racebrook Tract) combine to make a wonderful wooded walking path/hiking trail great for anyone looking to escape into nature. The trail starts here. Dogs are permitted, on leash, so you can enjoy your hike around Race Brook with your pup. A complete trail map is here. 

Peter’s Rock Circuit, in Peter’s Rock Park (North Haven, CT) is the hardest out of these three trails. I wouldn’t recommend this if it’s your first hike ever, but if you’re a beginner building up to medium level hikes then this trail is perfect. There is some elevation, due to climbs ending with beautiful views. However, it is a park that can become overgrown, especially in the deep summer months. Go in spring/fall, or use this map to find your way around. The trail starts here. 

Medium Hiking Trails Around New Haven: Location and Details

The medium trails highlighted here are great for somewhat experienced hikers who are looking for a challenge. They’re spread throughout a few local parks around New Haven to give a bit a variety in recommendations. 

East Rock Loop in East Rock Ridge State Park (New Haven, CT) is by definition an urban trail in an urban park. East Rock park is smack in the middle of New Haven, and as such isn’t the most quiet or peaceful of trails. With that said, this loop is definitely a medium level as it takes you up to the tower at the top (you can drive to this tower if you don’t want to hike it), so expect some elevation.  The trail starts here, and you can find a complete map of the trail here. 

Yellow/Orange Loop at Sleeping Giant State Park is probably one of the most common medium hikes in the area. Everyone loves Sleeping Giant, so you’ll want to get there early if you’re planning to take this trail on – the park will be busy. Luckily, most people are headed to the tower trail, and not this one – so once you’re on the yellow/orange trail loop there will be less people around.  The trail starts here and you can find a complete trail map is here. 

Regicides Trail, in West Rock Ridge State Park (Hamden, CT) is the longest medium level trail listed here. But, it’s completely worth the distance (and with intersecting trails, easily made shorter if you want it to be). I love the rocks, the views, and the gorgeous pine forest – its actually one of my favorite hikes in the entire state. I highly recommend hiking this trail, and put together this trail guide so you can learn more about it before heading out. 

White Trail, in Sleeping Giant State Park (Hamden, CT) is definitely the most challenging medium hike listed here. It’s a great intro trail if you’re looking to challenge yourself and see if you’re ready for a harder-level hike. So, I wouldn’t recommend it if you’re a newer hiker or one whose just getting into medium trails. Save this for when you’ve put some miles on your boots already. But, when you’re ready it’s an absolutely stunning trail. The views of the area are spectacular and some of my favorite in the park. The trail starts here, and you can get the map here. 

Hard Hiking Trails Around New Haven: Location and Details

The two hard hiking trails around New Haven, CT – are just that, exceptionally hard (especially the Blue Trail at Sleeping Giant). Do NOT undertake these trails unless you are an experienced hiker who is comfortable with rock scrambles, and understands hiking safety. These are not trails you want to try out first if you’ve never hiked a hard trail before. Seriously, know what you’re doing before heading out here. 

Blue/Violet Loop in Sleeping Giant State Park (Hamden, CT) is probably one of the hardest trails in the entire state. The elevation is tough, but it’s the very steep, exposed rock scramble that makes this so challenging of a hike. Multiple people have died attempting this trail, so seriously – do not do it unless you know what you’re doing. With that said, the views are incredible and the experience unparalleled in Connecticut. So, experienced hikers should enjoy the challenge and feel very accomplished after hiking one of the hardest trails in all of Connecticut. The trail starts here. You can find a complete map of the trail here. 

NET starts in Guilford, CT (Jacob’s Beach). The New England Trail (NET) is a 215 mile journey from the CT Coastline all the way to Northern MA/Southern NH. You obviously don’t have to hike the entire trail – as it can be done in sections. The Guildford sections probably are more of a medium level than an hard one – but the distance of the entire trail definitely is what puts this into the hard category. Depending how far you go there can be some serious elevation to contend with. But, section hikers can take it one section at a time and start at the beginning, in Guilford, CT. The trail starts here and you can find a complete trail map is here. 

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Hopefully you’ve found these 9 best trails for hiking in New Haven, CT useful. If you’re interested in other hikes in and around the state check out our hiking adventures page. For additional recommendations, check out the book 50 Hikes in Connecticut for even more guides to local hiking grounds. 

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