Aug. 22, 2023

Hiking Connecticut with “Jester” Section Hiker

Planning section hikes can take a lot of work. Luckily, every section hiker out there has a go-to podcast to help with that planning. Julie Gayheart hosts the “Jester” Section Hiker podcast and there is no better resource for anyone interested in...

Planning section hikes can take a lot of work. Luckily, every section hiker out there has a go-to podcast to help with that planning. Julie Gayheart hosts the “Jester” Section Hiker podcast and there is no better resource for anyone interested in section hiking the Appalachian Trail. Today, Julie walks us through what it takes to hike the Connecticut section of the trail. 


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Note: This transcript was generated by with light human correction

MILLS KELLY: Welcome to The Green Tunnel, a podcast on the history of the Appalachian Trail. My name is Mills Kelly, and I’m your host. As you might know, I’ve been section hiking the Appalachian Trail for the last 50 years. Every year I knock off another section or two and eventually, I’ll have hiked the entire AT. 

KELLY: Planning section hikes can take a lot of work. Luckily, every section hiker out there has a go to podcast to help with that planning. My friend Julie Gayheart hosts the “Jester” Section Hiker podcast and there is no better resource for anyone interested in section hiking the Appalachian Trail. Jester completed the Appalachian Trail in July 2017 after 12 summers of section hiking. 

KELLY: Today, Julie walks us through what it takes to hike the Connecticut section of the trail. The episode we are about to share with you covers the terrain, trail highlights, towns, covered bridges, and more! I hope you enjoy this episode of “Jester” Section Hiker and will check out other episodes of this excellent show.

JULIE GAYHEART: What is happening everybody? Welcome back to the jester section hiker podcast, your premier podcast with the spotlight on Section hikers and I am your host, Julie jester Gayheart. We are going to take a trip up to Connecticut, which is the gateway to the New England states. And we're going to talk about Section hiking through Connecticut today. But before we get to that, I just want to say give a shout out to everybody that is in the chat over on the Julie gay Hart YouTube channel. At Roger in the chat says Connecticut Yes, I have been waiting on this episode, planning that section this fall. So Roger, you shall wait no more. Let's go ahead and get to it. Connecticut is known as the gateway to New England. If you're out on the trail for a long section hike and you start to reach the New England states, Connecticut, Massachusetts, Vermont New Hampshire bein the air starts to smell different. Things start to cool down but also the terrain starts to change. And you will notice that if you go out and take a week or so to Section hike Connecticut, 

GAYHEART: I am going to be referencing the 80 guide pages 161 through 170. And I'm going to pull those up here in just a second. So you guys can see that if you are watching the video version. I'm excited because I am actually going to go section hike Connecticut again, because I feel like I missed some things on my first round. I have not been through Connecticut since 2015. And there are it's just, there's so much to see and do when you are section hiking the 52 miles that are in Connecticut, you will see all this checklist that I am recommending if you want to section hike Connecticut, that you absorb it take advantage of everything that Connecticut has to offer. But you also book in your trip by starting in New York and ending in Massachusetts. And that will give you 50 Or excuse me that will give you 68 miles instead of 52 miles. 

GAYHEART: And I want to pull up the 80 guide if I can make it work. I think I couldn't make it work on here. And the reason I suggest that you start in New York, a city that no one talks about rarely that I've heard in New York is Pauline paw L I N G Pauling New York has all the amenities that you need. You can get started there you can spend the night there and you could start you guys at the famous if you guys have watched anybody's YouTube channels if you've looked at at pictures of New York, most section hikers and thru hikers always take a picture of the at railroad station where you could take the train into New York City and everybody's always sit on the benches there or the big Long Bay lunch that they have at the New York trail station. And I recommend you start your section hike there. 

GAYHEART: You can get to Pauline, New York, you can spend the night there, you can get a shuttle or Uber, you can actually take an Uber from Pauline to the railroad station parking area. Take pictures, have an awesome time, get boots on the ground in New York, and then start your section hike. The next thing on the checklist is how are you going to start this hike it again, I am considering these episodes that we are hiking north and you get there. You start at the railroad station and you guys I would almost say you don't need if you're gonna backpack the 68 miles. You only need one to two days of food depending on how many miles a day that you are going to hike. Because in Connecticut, there are road crossings to towns that you could you have easy access to. In other words, I'm not sure when I'm going to hike Connecticut again it might be next summer. 

GAYHEART: I am going to start at the railroad station and I'm gonna have a day or two of food and you guys I am going to have fun because there are so many towns covered bridges, hot dog states places to eat. And we're going to hit that here in a second. Chris brought up a good point. I'm so glad you're all here because you can remind me of these things. Right before the railroad station is the DOVER oak. Now there are two huge oak trees on the Appalachian Trail. The first one that you're gonna see is the kefir oak or the kefir oak, which is just north of Perrysburg the Dover oak, which is it looks like two miles before actually you could get dropped off right at the Dover oak it looks like which is two miles prior to the at railroad station. And the 80 guide says the Dover oak the door side of the road, the largest is this says is the largest oak tree all the at the girth is 20 feet by four inches and estimated to be over 300 years old, Do not drive or park are the roots of the oak as doing so can impact the health of the tree. 

GAYHEART: So according to the 80 guide, it is the largest oak on the Appalachian Trail. But you do have the kefir oak or the kaffir oak that is back in Virginia. So again, my recommendation get yourself to paly, New York, get yourself a copy of the 80 guide it start at the Dover oak and work your way north. So you've got the Dover oak, you've got the railroad station, you're already having a good time. Your first stop, that I recommend that you do and not miss this is bulls bridge. There are several towns and row crossings that you're going to come across. In this first one, you're going to come to a road intersection, I believe it's a gravel road at bulls bridge is your first covered bridge, that you're going to have an opportunity hiking on the 80 going north to go off the trail bulls bridge is off the trail. 

GAYHEART: But there's a covered bridge, there's a store, it's an awesome place. I think sometimes they have a hotdog stand there depending on the time of year, the very first day, you have the opportunity to see the largest oak tree, the famous New York railroad station, bulls bridge, and you've already had an opportunity to eat. And you know, you're gonna have breakfast before you head out on the trail that first day. So you're not going to have to carry that if you go down to bulls bridge and you go to the country store, you're going to have an opportunity to give meal there. So right there the first day, you've eaten breakfast, you're carrying your snacks, then you have an opportunity to go down to the country store depending on the hours and the time you get there. So that first day you may not have to carry anything with you but your snacks and dinner that night. It let's go back to the 80 guide. 

GAYHEART: So that's your first day you guys and it is packed with all kinds of information, all kinds of things you could do add you have your hiking, so we haven't even talked about the hiking so you're gonna see the Dover okay, I've got the map pulled up here, which is a pretty good map that gives you an indication of what you're gonna do all this first day, you're going to see the Dover oak, you're going to see the famous railroad station, you're going to continue on and you're going to cross into Connecticut and then you get to bulls bridge It says here that bull's bridge is point three miles east off the trail, it is 100% worth it. And I totally recommend it. That could potentially be your first day in Connecticut. And by the time you do all that you are totally going to be exhausted. So that first day is already packed. And you are hitting your way into the New England states where you guys are going to come upon some interesting terrain in that 68 mile section in Connecticut. 

GAYHEART: And what I mean by that is the terrain. Once you cross over from New York and Connecticut, you're going to kind of weave back and forth. I'm not sure how many miles, New York, Connecticut and then finally you're going to enter into Connecticut. And you're going to go along the Housatonic River, and you're gonna think like, golly, this is like, this is awesome. I'm walking along the river, I make Connecticut you know, the trades not too bad. But then, as you get into day two, day three, day four, and you'll notice on the checklist, I have some particular highlights, I guess odd here. So the terrain, just like Georgia, I said, Georgia, the terrain is going to trick you the terrain, and Connecticut is going to trick you as well, because you are entering the New England states at you are starting to get into the terrain, that is going to give you an idea of what you're going to hit in New Hampshire and Maine. And that actually starts with Caleb's peak. So you're going to hit three different areas, probably depending on your mileage, and what you're going to be doing. either the second or third day that you are out there, you're going to hit Caleb's peak, you're going to hit St John's ledges, and then you are going to enter sages ravine. 

GAYHEART: So Caleb's peak is amazing. You do have to work hard to get up there. And once you get up to the peak, you can look out you can celebrate, and then you're going to come upon St John's ledges and St. John's ledges is this rock formation that you have to weave in and out of, I will tell you a little story about jester going through St. John's ledges. So when you get to this rock formation, there are white blazes on the rocks. And there are double blazes that tell you to go one way or the other. And I was totally not paying attention when I started to truly enter St. John's ledges area, and totally went the wrong way it was climbing this rock formation. I don't even know where I was going. And I probably went, I don't know, maybe two or three football field links and realize that I was not all the 80. 

GAYHEART: So I had to climb my way back down and try to figure out where the white blazes were. And then continue on my way once I found my way, these ledges they're really really steep rock steps, all boats that you have to go down and it's going to give your legs a really good indication of what is ahead and if you have not been out on the trail and you have not conditioned your legs to terrain that is going to take you straight up and take you straight back down at Big Rock stepdads. 

GAYHEART: You are going to be surprised when you get to that area. But Connecticut you guys is one of my favorite states because as a section hiker, it gives you a very good taste of all of the 80 you get a taste of the southern Appalachians, you get a taste of walking flat or all along the Housatonic river. And then as you are making your way toward the middle of the state and toward Massachusetts, it gives you a kick at the tail of what is to come in New Hampshire and Maine. So once you make your way through St John's ledges the next thing you can look forward to is sages ravine and you guys sages ravine I can't even describe it. It is it's almost like this mini ravine and you're walking north in the ravine for the most part is on your left hand side. 

GAYHEART: And if you are hiking there you are doing this section in the summer. You have several opportunities to swim and hang out in the ravine. You guys I can't even describe it. So it is a couple miles long if I'd be more than a couple of miles long, and you're walking along this ravine, and there's just swimming holes, and rock formations, it is not easy terrain, it will beat your feet up. But you're gonna have a great time going through there. And once you get through sages ravine, you will encounter Bear Mountain. And you guys, there is a Bear Mountain in New York. But this Bear Mountain, I got another story for that too. 

GAYHEART: So Bear Mountain in Connecticut, Sage's ravine kick by tail and Bear Mountain kick by tail. Bear Mountain is not bad hiking north, so you work your way up, and there's this huge rock pile, would you get to the top of Bear Mountain in Connecticut? And would you start to go down the backside of Bear Mountain, it is like straight to I mean, it is I can't even put my head the angle that this mountain is. And I just I had no idea. And I didn't know what to expect, or what was covered it go way down the side of this mountain, it was like I was holding on for my life. Because you feel like you're just gonna slide like you just, you know, you're at a sled and you're gonna slide down this mountain. And it was tough, it was tough, I almost wish I would have gone south, because I prefer to go up instead of go down, you know, steep terrain, but can't do that all the time, depending on what you have going on with your schedule. So just be aware, you don't want your pack to be real heavy. 

GAYHEART: When you're going down bear about and again, you guys, Connecticut, it's just packed full of amazing things. I mean, I can't even describe what you are going to see as you go through Connecticut. So again, you're gonna start if you do the 68 mile section, you're gonna start at the tail end at the northern end of New York, you're going to have a great few days. Again, I do not recommend carrying more than one or two days of food. Because once you get, you know hitting these highlights, you've also got several towns that you are going to encounter where it is easy access to get to these towns, whether you're to use a shuttle driver, whether some of these towns, you can use an Uber. 

GAYHEART: And in some of these towns, you may want to utilize the services that they have. You may want to spend the night you may want to resupply. There's so much in Connecticut, it's almost like you want to take your time and not rush through Connecticut and spend a night at each one of these towns. You could actually day hike Connecticut, no problem. If you want to use shuttle drivers or slack pack Connecticut, not an issue. What I would do is take a look in the bull's bridge area or maybe at the Saulsbury area and see what hostels are around in those particular towns. And maybe you want to Slack pack that whole section because you want to spend the night and towns and things like that it again, my recommendation is to contact the hostels in the area, contact the shuttle drivers in the area and go from there. And it's kind of like sky's the limit when it comes to Connecticut? 

GAYHEART: I did have somebody reached out and asked me Would it just be easier to pack 567 days of food and carry all of their food through Connecticut. I actually think it would be harder there's no reason to carry all of your food through Connecticut because if you're like me you want to see the town's you want to eat in town you want to utilize the services. You want to hit the highlights you want to see the covered bridge in bulls bridge. And I just think it's not necessary. That's just not necessary to carry 567 days of food just because you don't want to resupply take advantage of not having a heavy pack. So I think I left off all Bear Mountain and you guys as you get to the northern part two of my favorite places are mount race and the summit of Mount Everest you guys the terrain mount race. It starts to get rocky it starts to get what I call leji You're gonna have a lot of rock faces and ledges. 

GAYHEART: But make sure make a note right now. You either want to have lunch I would say plan your itinerary around having lunch on Mount race and then going from Mount race You've got a nice little climb, you want to make sure your bellies die so full you've got plenty of electrolytes and fuel in your system, because the climb up to Mount Everest will remind you that you have entered the New England states on the Appalachian Trail but when you get up there you can celebrate have an awesome time. And then on the northern end of that, you are going to be getting into Massachusetts. And if you are going to finish this section, you are going to get out somewhere around jug and road and that will give you a good 68 miles of going through Connecticut. Tons of highlights in Connecticut. 

GAYHEART: Dover oak, railroad station, bulls bridge, Caleb's peak St John's ledges sages ravine, the wonderful Bear Bear mountain to climb up and I'm going to call it the climb down. You've got mount race, you've got Mount Everest, which is absolutely amazing. tough climb. Very, very tough climb and steep. If you're going north and you're heading down to jugan Road, if you're going to end your section hike there it is a steep down, but well worth it. And you guys just take your time when you go to Connecticut utilize the towns I've got the towns on the checklist. Bulls bridge can't Cornwall bridge falls Village. One regret I have in walking through or hiking through Connecticut in 2015 is I did not spend more time in falls village. There are several places to eat. There are several places to stay. And you can find all of that information in the 80 guide it let's flip back over there real quick. Because I do want to flip to toward the end here you guys I've just pulled up like they're in Cornwall, I've looked at on The 80 Guide. 

GAYHEART: There are several places to stay. You've got the hitching post motel you've got the Cornwall in. You've got a package store there. There looks to be the bearded Woods I've actually heard quite a bit about this place. They do shuttles it says they are open may 1 Through October the first they do shuttles any distance. I want to get toward the end of our hike here. Falls village that I mentioned there's pizza places there's laundry bats. There's the Falls village inn and tavern. There's just too many to talk about. And like I said I do regret not spending more time in falls village. There is Saulsbury Connecticut on the northern end. I do remember go to the Saulsbury and getting ice cream. So put that on your list. 

GAYHEART: And this is something else I noticed in Saulsbury they have what they are calling a hiker square. And Chris I'm not sure if you're still in here but I have not been to this hiker square that did not exist in 2015. So I don't have a lot of information about that. But you guys when I go back through I'm gonna go through and see what that is all about. So you guys Connecticut. If you're looking on the map, it's 52 miles and there is some type of Connecticut challenge. You know how they have the four state challenge. In the southern states the four state challenges 42 miles the Connecticut challenge would be 52 miles and I have heard of some crazy hikers doing that 52 miles within 24 hours but if you plan to do if you plan to book in the trip where you're going to start in New York that northern end of New York at the railroad station there and you're gonna go north all the way past mount race all the way past Mount Everest and end there at Jug End Road that is going to give you 68 miles and packed in between there are I'm gonna go back to the checklist here several towns, several places to resupply. 

GAYHEART: I mean Connecticut, you guys, I pulled myself up I'm ready to go back through Connecticut myself. But yeah, so you guys, Connecticut, you got to be careful. Because Connecticut remember it's the gateway to the New England states. And what I mean by that is, depending on what time of year will depend on what you are carrying in your pack. So I went through Connecticut, the end of July the beginning of August. And then it was summer. I didn't have any issues. The one thing I will say it is cooler at night, you can start to feel that cool air. I have had some questions on what to pack in the New England states. And you guys, I bite, do a separate episode. All that because as section hikers, we can kind of plan around whether you can plan not to go to the New England states when you don't want to hike in the snow. When you don't want to hike in the spring because the spring can get kind of it could get kind of sketchy when you want to go. 

GAYHEART: And Chris says he's going in the fall, so he could see the fall leaves changing. And I'm telling you right now I'm excited for you, Chris, because going through say I can't imagine going through sages ravine in the fall. What an amazing, awesome trip. That would be. So you guys, we've packed a lot of information into 52 miles. If you're only going to do Connecticut, it's 68 miles. If you're going to add on hopefully I've talked you all into going to the Dover oak. Well, actually Chris talked to sin to go into the Dover oak, and then hitting the railroad station and then you guys, you're gonna hit Bull's bridge, you're gonna hit several tailed Caleb's P St. John's ledges, sages, ravine, Bear Mountain mount race, Mount Everett, and then you will have completed your hike of Connecticut. 

GAYHEART: Roger says our family is having a cookout today to get our details wrapped up for our Maryland and West Virginia section next month. We will also start our planning for our Connecticut section this fall. Want to hit the fall foilage it Yes. Roger 100% All that again, I'm jealous that you guys are going to be able to hit that in the in the fall. I cannot imagine what that's gonna look, I'm visualizing seizures ravine right now at the top of Bear Mountain in the fall. That would be absolutely amazing. All right, you guys are gonna wrap this up. We do have a couple people in the chat here. 

GAYHEART: I do appreciate you joining on this episode. I do have a special episode coming up. I'm interrupting the Appalachian Trail section hiker series. So we can have on Chica and sunsets from Chica and sunsets hostel down in Georgia, they are wrapping up their north bound season. And I had reached out to them earlier this year to see if they wanted to come on the show. And we agreed that they would come on as they wrap up the door throughout seasons. And not only are they going to be shared about their hostel, and what they've seen this northbound season what's happening with the hikers out there in the 20 2380 through hiker section hiker season, they are also going to be talking about their slack pack specials or options that they have at their hostel in the fall, which I think is totally awesome. So I am going to leave it at that. I do not see any more questions in the chat. I do appreciate you guys coming on. I hope I hope I hope that you guys are excited now to hike Connecticut, which is packed full of ledges, climbs, food resupply, plenty of towns, places to stay covered bridges. I really appreciate you joining me on this Saturday morning. no notice whatsoever, but somebody you showed up, and we've had a good time talking about Connecticut. 

GAYHEART: All the checklists. All the information for this episode can be found in the description on YouTube. It can also be found in the description or the show notes wherever you are listening to the audio version of the show. I'll leave it with this you guys Chris says he might need a pocket hang glider to go now bear bouton and he's got everybody laughing in the chat. All right, you guys once again, episode number 157. That is a wrap on Connecticut. Thanks for listening everybody. Be safe out there as always in happy section hiking.

KELLY: The Green Tunnel is a production of R2 Studios at the Roy Rosenzweig Center for History and New Media at George Mason University. Jeanette Patrick and Jim Ambuske are the executive producers. Thank you to “Jester,” Julie Gayheart for sharing today’s episode of “Jester” Section Hiker. At R2 Studios we’re on a mission to democratize history through podcasting, and we invite you to join us. So, head to and click on “Support Us” to help us make the best history podcasts out there. That’s it for today. Thanks for listening and we’ll see you again soon!

Julie Gayheart

Julie Gayheart (Jester) completed the Appalachian Trail in July 2017 after 12 summers of section hiking. Julie is an educator by day and hiker at heart. Jester loves to talk trail and on this podcast you will hear amazing stories and experiences from other section hikers with a love for the trail and passion for hiking.