West Rock Provides Respite from City Life, Sort Of

Sometimes, when you’re feeling a little blue, the answer is not, in fact, six more hours of The Office. Sometimes you just gotta, I don’t know, try.

“Y’know what I should go outside today.”

But then you’re all “I don’t want to got to East Rock again. I always go there. I should do something new. Change my life. Change who I am.”

Uh, okay, well maybe just check out West Rock. You can change who you are tomorrow.

I’ve lived in New Haven for eight years and I have hiked East Rock probably a hundred times.

I’ve hiked West Rock THREE times. And every single time I was like what the hell trail is this where am I going. It isn’t obvious like Giant Steps where you can just wander up, have a nice picnic, etc.

Yet West Rock somehow feels more disconnected from the city. When you’re hiking the trails, it feels more like hiking than just walking in New Haven up a steep rock thing with 200 other East Rockers even though you’re all inexplicably wearing Converse.

It feels like you’re actually in nature. If nature had motorcycles in the distance.

So I put pants on and I got out there and tried to have a nice hike.

Starting at the Base

I checked the map and it seemed like best spot is behind Whalley Ave near the base of the ridge. So first step is to obviously fill your stomach with the giant omelettes from Lena’s or Bella’s.

Next, make your way over to the West Rock Park Playground (https://goo.gl/maps/qqzAXAMzgmq83VG17). That’s where I started. This is the trail I took:

Annotated Trail Map
I’ve used my impressive Photoshop skills to help you see the trail I took.

The full trail map (which you should have when you go hiking!) is here: https://www.ct.gov/deep/lib/deep/stateparks/maps/WestRockGPS.pdf

It starts in a baseball field and you might notice that somehow the baseball field includes trail makers so you’re already on the trail! Well done, you’re hiking! Time to go home and eat some more candy.

OK but if you really want to hike what you’ll go is make your way to the far right part of the field towards the woods. Yes, there’s probably spiders in there, but maybe they’re friendly socialist spiders, this is a Sanctuary City after all.

But that’s where you’ll find the green/white trail, which is where you begin.

Behind baseball field
Yep, that’s right, in the creepy dark area

You’re gonna follow that weird trail with its overgrown vegetation and totally unmarked side trails that honestly who knows what’s going on there, until you hit the larger Green trail, and then you’re gonna take a right.

At this point it’ll feel more like a regular hike with a proper trail. You’ll still maybe hear some cars and see some housing to the right, but you’re on the way!

Keep taking Green for a bit it’s fine it’s pretty but I mean I didn’t take any pictures how great could it be. You’re looking to find where you meet up with the Red trail up to the summit. On the trail map it shows a little grey trail connecting them. I dunno, I felt like I just intersected with Red and took a left towards the “uphill” part.

Are these vague directions helping? You’ll figure it out.

Up the Red

If you’re on Red and you’re going up, you’re doing great. If you missed red, I don’t know, I’m not a sherpa, maybe hiking isn’t for you.

Up the Red Trail
If you’re going Up, you’re good.

The Red trail will take you up to the eastern summit where you can view the city below. It isn’t quite the Giant Steps of East Rock in terms of pure vertical climb, but it’s a solid uphill climb. Something about consulting your doctor before attempting strenuous exercise?

On the way up you’ll encounter a few vistas. You’re definitely stopping just to enjoy the view and not because holy cow you’re out of breath did you always used to be this out of shape and what happened with getting in shape this summer anyway boy did that not happen.

Vista from Red Trail
The view… *huff*… is… not bad… *breathe*… halfway up.

For some reason it keeps going but luckily this isn’t East Rock and nobody can see that a human being can sweat that much.

Red Trail Keeps Going
That red trail marker means you aren’t going to die here!

The Summit

After some amount of time, probably 20 minutes, probably less, you look pretty athletic (and stylish!), you’ll find yourself at the summit.

In a nice… parking lot.

But turn around and you can view the entire city from here.

New Haven from West Rock

OK, that’s quite enough nature for today and these video games aren’t going to play themselves.

Blue All the Way Down

Sure, you could take the Red trail down and that would be fine. But that would be boring. You were just on the Red Trail! You’re not a boring person, are you? No!

The Blue Trail is behind the weird Mini Parthenon Picnic Area. You’ll recognize it when you see it.

From there, you’ll get one more chance at a vista before you descend:

West Rock Vista
No way to fall off this!

The blue trail stays on top of the ridge, for the most part, and sticks close to the road, which is nice, because the thing you most want to think about when hiking is traffic.

Eventually, you’ll connect with the blue-yellow trail, where you can either go left, back down towards the entrance, or go right, which leads to the Three Judges Cave which is basically just a boulder with a plaque on it.

Having correctly chosen left, you descend the mountain down yellow-green. Here is a nondescript picture I took:

Downhill on Yellow-Blue

Just keep going and you might even see a couple humans.

Here is a picture looking down.

Oooh, more trees!
Not pictured: Some teenagers nearby smoking reefer cause I’m not a NARC even though I know I 100% look like one

Anyway keep walking and you’ll end up where you started: The weird baseball field that is technically part of the trail.

West Rock from Baseball Field
I was just there!

Y’know what? You’ve already seen the pictures. Really, I feel like that counts like hiking.

Great job. You did it.

My experience with West Rock was:


  • Feels more like “real” hiking than East Rock
  • The overall loop has a better length to it where I feel like I exercised (with East Rock it feels more like a jaunt than a hike)
  • The views from the vista are nice


  • You have to go to West Rock
  • Some of the trails are pretty close to the road and makes you feel not-at-all in nature
  • Picnic area in summit is… mostly a parking lot.

Go check it out and let me know what you think? Like it? Love it? Happy enough to look at pictures?


Don’t forget to check for ticks.

4 thoughts on “West Rock Provides Respite from City Life, Sort Of”

  1. As a newbie in town, I love your blog and your suggestions, including this one – which I plan to do (weather permitting) this weekend or next. Thanks for the brunch tips! Also, a great app for hiking is “AllTrails”, it downloads the map and uses GPS to track where you are on the trail. Keep up the great work!!

    • Thanks, Maria! Does the AllTrails app have a free version for that feature or do you have to pay for premium? I felt like I downloaded it at some point and I needed to buy it to get the “good” features but I may remember incorrectly.

      • I believe that feature is free, but I couldn’t tell you for sure. I’ve had the app for a while, and I highly doubt I would’ve paid for anything. And there are trails from all over the world! The maps are pretty accurate too. You may laugh, but I got lost in East Rock and the app put me back on the trail (which I must say, some of the trails there are not fully marked). Anyway, try it out and enjoy! Thanks again 🙂 I see you have a feature to buy you a coffee, I’ll def send one your way 🙂

  2. I guess I’m the Bizarro version of you, Josh. I graduated from Southern last year, and have dozens of west rock hikes under my belt. Journeys up East Rock for us were sporadic, dainty little luxuries. West certainly is rustic, but getting to look at the Sailors Monument watching over the city and the ocean is probably my favorite view in the city (aside from the view of the warm foyer at Modern after waiting in the cold for 45 minutes).

    (P.S. First time commenter; discovered you through the New Haven subreddit and already a big fan! I moved to Boston after college and have been up here for about a year, but the blog has been a great way for me to still feel immersed in my former home. Keep it up!)

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