Hiking the Blue Hills Skyline Trail (End to End)

Saturday was my second solo hike and possibly my hardest hike ever. It was definitely my most mentally difficult hike. I truly enjoyed the quiet time alone with nature and my thoughts, but there were a handful of times when I could have used some motivation or even just some commiserating.

I intended to let myself sleep as late as I wanted, but I woke up raring to go just after 6am. I forced down more food than I ever want that early in the morning – coffee, oatmeal made with almond milk instead of water and a dollop of peanut butter, and a hardboiled egg. I was starving almost immediately into my hike last weekend, so I wanted to start off nice and full but not stuffed.

20190803_084230It only took me 20 minutes to get to the Quincy end of the Blue Hills at that hour. I had decided that since I was going from the Canton end to the Quincy end, I’d park my car at the finish so I’d have it there with AC and clean clothes immediately available, and also so that I didn’t stink up anyone else’s car. After I parked, I called an Uber which was right around the corner, and paid the $12 (highway robbery, but whatever) for him to take me to the other end of the Blue Hills. He dropped me off at the Park & Ride lot on Route 138. There are some trails that head west from this lot to Little Blue Hill, but I couldn’t figure out which one to take and my AllTrails made was only for the official Skyline route, so I decided to skip that tiny section and just start heading east.

First, I had to cross 138, which is a very busy road. There were yellow hiker signs warning drivers, but no crosswalk, so I had to dart across the road. The trail was easy to notice from the road, and it went straight up almost immediately. I didn’t pass anyone at all in the half-mile it took me to reach the summit of Great Blue Hill. There were great views south, but it wasn’t until I climbed the top of Eliot Tower – which looks a lot like Wright’s Tower in the Fells but was open and climbable – that I got 360-degree views, including the Boston skyline and the Harbor Islands. There were a ton of people up there already, around 8:30, and I just wasn’t into the crowds so I snapped a few quick photos and hopped back on the trail.

Boston skyline from the top of Eliot Tower

The trail immediately and steeply descends after leaving Eliot Tower, and my knees and feet were already so unhappy with me for keeping my poles stowed away. In fact, I didn’t start using them on the steep descents until more than halfway in, because my right knee was on fire (it was fine as soon as I started using the poles). An older couple coming up one of the steep parts I was going down even said, “Surprised you’re not using your poles on20190803_111426 this! We would!” I know, I know… Lesson learned.

The rest of the trail continued with steep climbs and descents, many on completely bare rock that required scrambling to get up and butt-sliding to get down. It was a fun adventure, and I was glad for it – having assumed nothing this exciting and challenging could exist so close to Boston.

In fact, this was a LOT harder than the Middlesex Fells. There were so few flat parts in comparison, and the climbs were much more steep and scrambly. It was also a lot busier between Route 138 and the Blue Hills Reservation headquarters on Hillside Avenue, where there was actually a nice crosswalk across the busy road. Once I crossed it, I saw about a tenth as many people on the trail. Everyone was going in the opposite direction – I didn’t pass anyone until almost the very end, and no one passed me. I checked in with my parents around the halfway point to let them know I was doing great, because I realized this was going to take a lot longer than I had anticipated due to the elevation gains and losses. And also because the migraine from last hike was so miserable that I was determined not to overdo it in any sense of the word. I brought my new 3-liter reservoir (previously used a 1.5-liter and carried two 30-ounce water bottles) plus a bottle of electrolyte water, and only ended up drinking half of each of them because I didn’t want to run out but also didn’t feel like checking to see how much was left.

Around 2.5 hours in, I was starving and stopped for a Clif bar. I noticed that it had caffeine, and I definitely got a little burst of energy afterward. Whether it was the caffeine or just the calories or both, I think I will definitely invest in more of those for long hikes! It’s like an energy gel for long runs, but less nauseating and actual food. I can never eat actual food on long runs but can definitely eat on hikes! That wound up being the only food I ate all hike, although I could have and probably should have had one of my turkey jerky sticks toward the end of the hike.


The last mile is almost entirely flat, with some very gradual downhill at the beginning. You actually finish the hike by walking past these gorgeous ponds filled with lily pads. From here, you can see the road and the parking lot. As soon as I got to my car, the off-and-on sunny skies turned dark and a few drops fell, but it was just a tease. Those few raindrops were it, and then the sun came back out in full force. Oh well. I used some baby wipes to clean up, changed into clean shorts, a tank top, and flip-flops, and let my parents know I had survived. It had been 4.5 hours and 7.5 miles.

I was totally beat, but realized I was 3 minutes away from Widowmaker Brewing, which I’ve been dying to try. So I went, had a flight while I chatted with the bartender and the couple next to me who wanted to hear all about my hike, grabbed a hot dog from the food truck for the road, and finally got home 8 hours after I left. Chip of course wanted to go out immediately, but it was a tortuous walk with angry blisters already forming on both my feet. My boots and socks are great, but it was all that time with my weight in my toes/balls of my feets on the steep descents that did me in. I ripped a few open so that they’d have all week to heal, because my dad and I are planning to hike Mount Greylock (the highest point in Massachusetts) and potentially Saddle Ball Mountain (the second-highest point in Massachusetts) next weekend, and it’s a tough hike of 5-8 miles depending which trail we take and which peaks we bag. Walking on Sunday was miserable, and I didn’t even hit 10,000 steps. I also napped HARD for two solid hours in the afternoon. Walking still isn’t super pleasant today, but I know everything will be fine by the weekend. And I will use my poles a LOT more on my next hike!

(click any photo to enlarge)


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