We rented a nice Vrbo in Great Barrington, MA as a base camp for this trip.
1 May 2026
We did 2 small sections and scouted future hikes while we waited for our guests to arrive later that evening.
Lake Buel Road to MA-23
Easy gentle introduction to hiking with soft pine needs on the trail.
Houstonic River to Holmes Road
Slight up and lots of downhill at a sideways slope.
We met 2 really nice section hikers on the way down the mountain and stopped to talk with them for about 15 minutes. One guy had 2 knee braces and was trying to avoid have a knee replacement.
2 May 2026: Lake Buel Road to Homes Rd: 4.6 miles
Dragonfly, Nature Nut, Lockdown, Dirigo, Python
Stopped at the Tom Leonard shelter for a nice break. There was a good water source near the shelter and the privy was very clean.
Met a nice group of female section hikers from CT.
Lots of ups and downs today with way too many rocks.
I think we broke our niece! She said she would need to review the elevation profile for the next hike before she was willing to commit to it.
3 May 2026: Guilder Pond to Jug End: 3.9 miles
Dragonfly, Nature Nut, Lockdown, Dirigo, Python
We waited until the rain stopped at the rental before heading to the trailhead.
When we got to the trailhead parking lot it was snowing! It was chilly at the start of the hike but we quickly warmed up once we started climbing.
The rocks at the end were brutal!
4 May 2026: Guilder Pond to unmarked trail to Mt. Washington Rd: 6 miles
Lockdown, Dirigio, Python
The hike up Mt. Everett wasn’t too bad and the descent wasn’t too bad either but it was very warm so we were shedding layers pretty quickly.
Saw a big pile of bear scat right on the trail but fortunately did not see any on the hike.
Seems like we stayed at the top of Race Mountain for a long time – the trail skirted the edge of the mountain so we got really nice views of the valley.
Met several hikers as we approached Sages Ravine. A section hiker named John had just been treated at the ER for tick bites.
Sages Ravine was absolutely gorgeous but the climb up was hard at the end of a very warm day. Our phones died so pictures of Sages Ravine are compliments of Lockdown.
Some time after Sages Ravine both Python and Dirigo ran out of water.
We were so happy to see the sign to the Mt. Washington Road but there was no mileage on the sign (0.8 miles). Fortunately, we met 2 hikers on the trail that confirmed that we were heading back to the AMC hut trail head parking.
5 May 2026: Beartown Mountain Rd to Tyringham: 6.4 miles
Dirigo & Python
It was a very warm day with lots of bugs and bogs! The trail was mostly gentle and it was nice that we could finally stretch our legs. The bugs were awful though!
Cobble hill was a pain because it was so hot but there was a wooden bench at the top where we finally could get a nice long break from the bugs.
The trail went through several fields and we have to go over livestock gates.
The end of the trail had lots of bridges because of the bogs and the bugs were bad!
6 May 2026: Beartown Mountain Rd to MA 23
Dirigo & Python
We actually got on the trail early today because rain was forecasted for around 11:30 AM.
Driving to Beartown Mountain Rd, we saw a beautiful barred owl.
Since the bugs were so bad yesterday, Python bought a new hat and bug net from the outfitter in Lennox.
The Chinese buffet is closed!!
We did not see anyone else on the trail today. We tried to keep a good pace despite the bogs, bugs, and rocks to beat the rain.
The descent from The Ledges was not fun.
We were so happy to make it back to the car before the rain!