Connecticut’s 20 Most Popular Hikes (According to Google)

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When you feel the call of the wild, you have to express it and get out into nature. In today’s world, you also have to figure out how you’re going to get to said nature. Which is why many people turn to Google before they go hiking.

We used Google tools to measure how many people are searching for different hikes in Connecticut every month. These are the most popular hikes in the state, the go-tos for people who are looking to get outside.

We then interviewed a number of local hiking experts to get their tips and tricks for each location. They are:

Rob McWilliams, from McWilliams Takes a Hike

Clare Cain, Trails Stewardship Director of Connecticut Forest & Park Association

Mark, from Hiking for Donuts

Rory Larson, Conservation and Program Leader, Steep Rock Association

Jay Willerup, President of Board of Directors, Friends of Heublein Tower

You’ve probably heard this a billion times by now, but before you go to one of these places, make sure you check out their latest COVID-19 advisory which we are linking to where available. Please consider checking out the #CTTrailslesstraveled hashtag on Instagram for less crowded hikes as well.

1. Sleeping Giant State Park

3,200 Monthly Google Searches

Latest park advisory here.

Photo by @ilovemoo

Rob: I didn’t go there for a long time because I thought it’d be quite suburban. I’ve been several times since, and it’s a great place. Some of the hiking is quite rough. There are some great views, particularly on the giant head/chin, and other parts of his anatomy. Some of the hiking is quite demanding, not for the faint-hearted. Some pretty steep slopes. It can be a little intimidating in icy or wet weather. You can great a half-day outing at Sleeping Giant.

It looks like a giant man lying on his back. It’s wooded, and rocky, like most of Connecticut. And it’s surrounded by low land. You’re kind of on this wooded, rocky hill with lower land around you. I don’t know how big it is exactly, but you get a good feeling of being away from it all. There are rough trails there, and there are also carriage road-standard trails, so there’s something there for everybody. There’s a stone tower that everyone heads for. The other thing to mention is that it was hit by a tornado a couple of years back, and it’s only just re-opened after that. Some of those trees I’m talking about may well be gone.

It’s a popular place, close to New Haven, not that far from Hartford, it’s got that nice name. There are also trails that most people don’t go onto, so you can have your own experience, you can do the popular stuff, or take those lesser-walked trails.

There’s also an old trap rock quarry there by the giant’s head, which is the reason why some of the trails are steep and intimidating because you’re dealing with the side of the quarry.

Mark: Not surprised this is #1. It’s pretty popular in Connecticut. It’s near Quinnipiac, so it’s overcrowded. A lot of the popular hikes, the earlier you start the better. I’ve definitely hiked it quite a bit. The one good thing about it is that it has all types of trails. If you’re a beginner, intermediate, there’s something for you. But it’s always crowded, it closes down quite a bit.

Clare: It has a ton of different trails. You can stitch together a hike of almost any length. The quinnipiac trail (?) runs through the park, and it’s one of the oldest trails in the state, which is pretty cool. The Tower Trail takes people right to the top of the park, and the tower is there (make sure you check that the tower is actually open). You get some great views of Long Island Sound and it’s kind of a destination.

2. Castle Craig

2,500 Monthly Google Searches

Latest COVID advisory here.

Rob: I was there once, it’s in what’s known as the Hanging Hills. There’s a legend of the black dog of the Hanging Hills, some strange dog some people claim to have seen in the area. It’s got a sort of mock-castle on top of it. You can get there by road, lots of people up there on a fine day. But you can move a short way away and you’ve got much less-traveled trails. I went there the one time because it’s on the Metacomet Trail, and that trail comes down from the Massachusetts line, and turns into the Mattabesset Trail, so it’s on the New England Scenic Trail. Great views over central Connecticut, it’s about 1,000 feet up.

Mark: There are a lot of different trails to get to the top and see all the views. You can actually drive to it as well. There are a lot of trails to get up to there, I always go to the East Peak. If you want a really good hike there’s a lot of elevation, there are certain points where it’s definitely pretty steep. You get a lot of different views, and once you get to the top, it’s one of the unique ones. You can see all of the outlooks, the rest of Hubbard Park and some parts of Meriden.

Clare: It’s in Hubbard Park, in what we call the Hanging Hills, which offer really dramatic views off of the cliffs there. They’re on a whole stretch called the Metacomet Ridge. It’s on the New England National Scenic Trail. It’s kind of one of those iconic spots in the state because you can see it perched up on the ridge from miles around. You can go over to West Peak, that whole ridgeline has great views too.

3. Hubbard Park

2,400 Monthly Google Searches

Latest COVID information here.

Photo by @sharneu_nemo

Rob: Everything I said about Castle Craig probably applies to Hubbard Park too.

Mark: We’ve been on a few different trails there. Castle Craig is the main one that I do.

4. Kent Falls State Park

2,100 Monthly Google Searches

Latest COVID info here.

Rob: Waterfalls, obviously, and they are beautiful. Very popular. On a weekend you’re going to have lots of company. It’s best to go after there’s been a decent amount of rain, and then it’s pretty spectacular. The whole area is beautiful if you want to go for a picnic or something. I wouldn’t really call it a hike, you can walk up the side of the falls, you’ll be done in an hour.

Rory: Beautiful, cascading falls that are very accessible.

5. Wadsworth Falls State Park

1,700 Monthly Google Searches

Latest COVID-19 advisory here.

Mark: I would say it’s a pretty good hike. Just over three miles, kind of a nice woodsy little hike. Once you get to the actual Wadsworth Falls, it’s a pretty good waterfall. If it rains the night before, it’s a good flowing waterfall.

6. Heublein Tower

1,700 Monthly Google Searches

Latest COVID advisory here.

Photo by @xxaprilmay

Jay: I grew up nearby, and whatever town you’re in, you lay claim to it. It’s a local icon. We lost my dad when I was 11, he was a businessman, but he also played a mean piano. His forte was jazz and ragtime, and the Heubleins built and owned the ower, and then the local afternoon newspaper owned it, and they used it as an entertainment venue. And my dad would be asked to come up and play for the guests. We never shared stories about it, but I’m trying to carry the torch so to speak.

The architecture is pretty cool, and it’s 165 feet tall. When it’s open and you go up to the top, you can see into New York, Mohonk Mountain, Springfield Massachusetts, Hamden, but you get some pretty commanding views. It’s a hike to get there, probably about 40 minutes. It’s the only park in Connecticut is a hike-in only. There are a couple of ways, one is through MDC Reservoir, and the traditional one is off of 185, and there’s a pretty challenging one that comes up from Avon. There’s a driveway, but the state has limited access to that because there’s no parking and it’s a very narrow road. Even with that, the average attendance up there is between 100 and 125,000 people a year, and they have to hike there. It’s a pretty staggering number. We as the friends group, the tradition has it is that the Heublein’s always had a guestbook, and we’ve continued that, when you go into the lobby we ask that you sign in. We just finished tallying last year’s people, and for the first time in 17 years we got all 50 states and 53 countries.

Rob: It’s on the Metacomet Trail, it’s a little west of Hartford. It’s worth saying the Metacomet Trail follows the top of the Metacomet Ridge, which is this volcanic ridge that runs right across Connecticut from the Massachusetts line down to the Sound. Heublein Tower is one of the highest points of the ridge, you’re at 1,000 feet or thereabouts. There are different routes to get up there. You can come from the north from a state park called Penwood, or from the south, from one of the Hartford Reservoirs. Quite rough in places, not an easy climb. The trails are kind of rubble. They can be quite hard on the feet. Once you get there there’s great views. I believe President Eisenhower agreed to run for president at a meeting at Heublein Tower. It was built by a German immigrant, I think. That whole area, Bloomington, Simsbury, towns like that, there’s some great walking there.

Mark: That one is very popular, I like to call it my weekday hike. If it’s nice out during the week it’s a quick two miles, and it takes you up to Hueblein Tower. It’s a cool little view, the tower itself is something unique as well. It’s pretty easy to moderate as well.

7. Devil’s Hopyard

1,500 Monthly Google Searches

Latest COVID advisory.

Mark: I did a hike here a couple of years ago. Very woodsy, typical Connecticut hike, there are a lot of cool bridges, there’s Chapman Falls there. It has pretty good vista views.

8. Pachaug State Forest

1,500 Monthly Google Searches

Latest COVID advisory.

Photo by @sayhimelissa

Rob: Apparently it’s big enough to backpack and spend the night there, but I haven’t been there.

Clare: The Pachaug is the largest state forest in Connecticut. It’s in the southeast corner, and it’s this large contiguous block of forest with a number of different trails running through it. The Pachaug trail is a loop trail through the whole forest, and we have some other trails we maintain. It’s a beautiful area, lots of ponds, streams, lots of local native culture in that area. That whole forest is also contiguous with state lands in Rhode Island, so you can either stitch together hikes that cross between states.

Green Falls Pond is a popular recreation area in the forest. A lot of trails kind of come to that point, there’s a trailhead there, there’s a campground there, there’s a beach and a pond there, and longer trails that kind of stem off from that area. There’s a ton of options for folks over there. The whole forest is really varied and beautiful.

9. Harkness Park

1,400 Monthly Google Searches

Latest COVID advisory.

Photo by @brianbiggs

10. Bear Mountain CT

1,200 Monthly Google Searches

Photo by @ehsan.ashik

Rob: I could talk about this one forever. It’s up there in the far northwest of Connecticut. It’s undoubtedly the wildest part of the state. There’s a plateau, it’s about 2,000 feet high, it’s covered in peaks and summits. Bear Mountain is the highest peak in Connecticut. It’s on the Appalachian Trail. Most people get to it from Connecticut Route 41. You have two choices, you can go straight up the undermountain trail, but by the far the best route is going up the undermountain trail, and then turn onto a longer trail called Paradise Lane, it’s a beautiful trail, it takes about an hour, it’s two miles of relatively easy but remote hiking. Then there’s a scramble to get to the top of Bear Mountain. You have to be reasonably fit to be able to do it. It’s not good in icy conditions. Once you’re at the top the scenery is fantastic. You can see Mount Greylock in Massachusetts, which is about 40 miles away, you can see the Taconic Plateau, if you go a few miles west you can get to an escarpment and see New York and the Catskills in the distance. Fantastic place. 

Like any good place, you’ll have company on top of Bear Mountain on nice days and the weekends, but during the week you might have it all to yourself.

Rory: It’s on the Appalachian Trail and the highest elevation in CT. A rock platform was constructed at the top to break a certain elevation barrier. It’s a gorgeous view looking over the Twin Lakes in Salisbury. If you’re looking for a peak with incredible vistas, that’s a good one. Sections of the AT leading up to it, such as Sages Ravine, are highly recommended

Mark: I have quite a few friends who’ve hiked it, and they tell me it’s the highest peak in Connecticut.

11. Talcott Mountain State Park

1,200 Monthly Google Searches

Latest COVID advisory.

12. Bluff Point State Park

1,200 Monthly Google Searches

Latest COVID advisory.

Photo by @mauro12

Rob: I was there a long time ago, it’s on the Sounds, or the shore. It’s nice, you’re by the shore, you get to walk woodlands to get to the Long Island Sound.

Mark: This hike is part of the Coastal Reserve in Groton. It’s a pretty nice walk along the water. If the water is out you can walk out to the rocks and along the bluffs and everything. For Connecticut it’s kind of cool and unique to see the water and bluffs like this. It does get very crowded, so go early.

13. Bigelow Hollow State Park

900 Monthly Google Searches

Latest COVID advisory.

Photo by @joyanddirt

Clare: The northern end of the Nipmuck Trail, which is approximately a 30 miles trail in the northeast corner of CT, and it terminates in Bigelow Hollow. There are also some loop trails there around some really beautiful lakes. There’s a number of different options. It’s really beautiful all season. It’s probably less visited than the other places on your list because it feels more remote up in the Northeast corner, so there’s kind of a rugged quality to it. It’s quite beautiful, people fish there, you can hike, you can camp. People do ice fishing up there in the winter. Kind of a full-season type of park that I would guess is a little less-traveled.

14. Chatfield Hollow State Park

700 Monthly Google Searches

Latest COVID advisory.

Clare: We have a trail that’s not directly in the state park. We have the Chatfield Trail, it starts at the state park parking area, and heads south from the park into the neighboring state forest. It’s a really cool trail. It’s really rocky and rugged, lots of glacial erratics. It offers a way to explore a little outside the park, but within the same terrain that makes Chatfield Hollow so interesting. There are also a number of trails within the park and it’s a beautiful park.

15. Farmington Canal Heritage Trail

700 Monthly Google Searches

Latest COVID advisory.

Photo by @jarvaelison

Mark: This is the rail trail that connects to a large part of CT such as Farmington, Southington, Unionville all the way to New Haven and even Massachusetts. Some areas take you along the Connecticut River or the Farmington River. Anytime you go it’s pretty busy, especially on a nice day. It’s a heavy biking trail. If you’re looking for a nice little walk, there are so many different areas to go.

16. Macedonia Brook State Park

700 Monthly Google Searches

Latest COVID advisory.

Photo by @vibertdave

Rob: Probably my favorite place in Connecticut. It’s near Kent, on the New York line, it’s a fairly steep-sided wooded valley. The Macedonia Brook runs through it. There’s a loop trail. People call it the Blue Loop, and it takes you over hills on either side of the brook. You get to ledges where you just look down the valley, you’ve got these wooded, rounded hills that are very picturesque. There’s a hill there called Cobble Mountain, and the best ledge there faces New York, so go there at the right time and you’ll have views of the Catskills. You can camp in the park in the summer months, I used to take my kids there when they were young, and it’s a great place to camp and wander the hills. Very very peaceful, beautiful brook. One of my favorite places.

Rory: An absolutely gorgeous, rugged tract of land with pristine streams. Great hiking with a diversity of difficulty levels. 

Clare: It has the rugged outer blue loop. Someone might be looking for a more challenging hike, that would be the way to go. There are a number of interior park trails. You don’t have to do that big outer loop, you can loop back into the interior trails. You get some nice views up on Cobble Mountain. That outer trail is called the Macedonia Loop trail and wraps around the park. You get some major differences in elevation and get some really beautiful views off to the west. It’s close to the Appalachian Trail over there.

17. White Memorial Conservation Center

700 Monthly Google Searches

Latest COVID advisory.

Photo by @haw529

Rob: I was there recently. I’m not an expert. There’s a long-distance trail called the Mattatuck Trail that goes through White Memorial. That’s what I walked. It’s a very nice mixture of sort of pinewoods, hardwood forest, and a lot of marsh and pond, a lot of birdlife. Fairly flat, and the trails are pretty good, so if you’re looking for a relatively easy walk it’s a good place.

Rory: Close to home for me.  Water resources are the real highlight – a vast array of swampland, wetland, beaver pond, and river. Unparalled birding opportunities, as well as the birding opportunities they offer They have an incredible length of boardwalk that goes around a lot of those water bodies. The trails are mostly flat, no real peaks or anything, but a pretty expansive trail network.

18. Steep Rock Preserve

600 Monthly Google Searches

Photo by @kcblakeley

Rory: Steep Rock was the original tract of land that started the Steep Rock Association. It’s just shy of 1,000 acres with several points of interest. It’s as close to wild land you can get in CT, as far as I’m concerned. There’s a huge tract of old growth hemlock forest, it’s kind of other-worldly. You don’t find forests of that age around here. It holds about 4.5 miles of the scenic Shepaug River. The town-owned Tunnel Road hugs the river for a considerable length.

When it’s open, you can drive Tunnel Road to its current terminus and get really close to the Tunnel, which is pretty high on the list of points of interest in Steep Rock. It’s 237 feet long, blasted out of bedrock. That’s really cool, and offers a nice respite in the summer for hikers. Huge icicles hand down either side in winter and spring. There are also ruins on site of an old vacation retreat called the Holiday House. It was offered for working women in the city who had pretty tough living conditions to come up for no charge.

There are nine different trails with a bunch of little connectors between them that aren’t named. There’s also a summit that overlooks an unique turn in the Shepaug River, called the Clamshell. It’s a pretty good ascent to the Steep Rock Summit. It does get a lot of use in the heat of the summer, holiday weekends, but there are 40 miles of trail nearby so even on the most populated days, you can get off on other trails and not see anyone for your entire time out.

19. Denison Pequotsepos Nature Center

600 Monthly Google Searches

Latest COVID info.

20. Farmington River Trail

600 Monthly Google Searches

Latest COVID info.

Mark: Everyone goes for biking, a lot of bird sighting, a lot of people do tubing there. It’s one of those easier walks along the river.

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