Explore Appalachian Trail: Massachusetts: Best Day Hikes - view hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

This month marks the 80th anniversary of the #AppalachianTrail, which passes through 14 states from Maine to Georgia. . With so many access points along its approximate 2,190-mile route, this trail is not only an excellent option for thru-hikers and section-hikers, but also day-hikers and those looking to escape into nature for a few hours. . To honor the Appalachian Trail, we have compiled a list state by state of some of our favorite day hikes along the AT. Check out this list for Massachusetts and help us celebrate the legacy and natural wonder of this trail!

Appalachian Trail: Massachusetts: Best Day Hikes Map
VIEW FULL MAP
hiking
5 days ago

1.17.19. A really fine, easy hike with a little bit of everything: forest, streams and open landscapes. Starting from the parking lot, we followed the blue acorn blazes counter-clockwise on the splendidly maintained trail (it was still obvious even at the higher elevations when covered in 2 or 3 inches of snow). The first half saw a bit of mild climbing. Beautiful open areas at the beginning and towards the end of the outing. If you haven't tried it and are are wondering, here are my stats as a guide:

Distance: 4.3 miles
Elevation gain: 577 feet
Moving time: 1:37:51

on Jug End Road

hiking
1 month ago

great hike, not much elevation, great scenery. excellent to do with the entire family!

Nice hike! Parking lot indicated works well. Leaves just fell on trail so it was a little tricky in spots, but overall pretty well blazed. Pine woods in the first mile is really nice as is the pond!

Park in the AT/Jacobs Ladder lot on Route 8 & 20, then use the blue connector trail to avoid walking along the road to the AT. Beautiful rolling trail through the woods, fairly easy grades. LOTS of mud currently (mid-Oct). It was a wet day with low cloud; views of the lake were only available once we were right on top of it.

I’m a noob to the AT, but this was the most difficult hike I’ve ever done! If this is “easy” I don’t want to know what a more challenging hike is like. It was beautiful - but tough.

Wasnt a bad trail. was foggy so views were bad. otherwise would have a bad view. summit was marked by cairn, with some decent outlooks along the way.

Great hike. I parked at Jug End road and began my hike there. Unfortunately I picked a rainy so, it was slippery and muddy, and the trails were covered by the mist. At least it was chilly and not humid or muggy. I originally wanted to hike all the way to Bear Mountain but once I got to Mount Race I decided to go back cause it’s a long loop. If it was a one way, i would’ve done it. A loop hike to Mount Race alone was a total of 12.6 miles and by the time I was close to my car I was so sleepy and hungry lol. I almost wanted to crash at the Glen Brook shelter lol which btw it’s a beautiful shelter. There’s an outback, fire pit, bear box, table with a bench and a creek nearby. I got one clear scenic view but others were misty. The wooden stairs bolted on the rocks are pretty cool too. I was surprised at how many through hikers I met along the way some coming from Maine and others from Georgia. They were real nice people. Other than that, it was an awesome hike.

5 months ago

Pretty wildflower meadows. Offset however by the fact that this is a full on rattlesnake preserve!

good hike but a few areas were really steep

Fun day and the pond is beautiful. That said, the trail map is poor. We stayed on the AT past the intersection with the Finnerty trail near the pond, and then thought we could go all the way around the pond counterclockwise and back along the eastern edge of the pond, but you can’t do that. Although it looks on the trail map like the Finnerty Trail runs along the edge of the pond and links up with the AT on both sides, it doesn’t. There are dead ends in between and it’s pretty much impassable. There is a way to go around the pond counterclockwise (which we eventually did) but you have to swing wide of the pond to the east.

Also, the trail map makes it look like you can return almost to the parking lot on the Finnerty Trail but you can’t. Finnerty Trail dead ends at Becket Road, and then we had to walk up the pond road, which is steep, to return to the AT. So the bottom line is, this is a nice area to hike, lightly trafficked, and the pond is really nice, but stay on the AT, don’t mess with the Finnerty Trail relying on the All Trails map.

Difficult to find where trail begins- parking area is about .2 miles from trail head. If you park in the Appalachian trail/Jacob's ladder lot, there's a .2 mile connection trail, marked in blue, across the road. It intersects the trail in the woods, hang a left. Otherwise you could walk on the actual road for nearly a quarter mile and catch the trail from there- which is why the Alltrails GPS directions will seem slightly off.

Hike is pretty much all uphill for the first half, but is very well covered. You'll also cross another main road on the way. Took us about 1.2 hours to get to the lake- definitely a moderate difficulty. Beautiful view once you're there. Looked like the muddy beginning portion of the hike had been fixed with raised planking. Nearly exactly 3 miles from parking lot to lake. Well marked, took 2 adults about 3 hours to complete out and back at a moderate pace.

Did this loop 6/24/18 as a training hike for a Yellowstone trip. Got a late start (1045). Knew thunderstorms were coming and was gonna cut it short after Mt Williams. Decided to do the entire loop regardless. Warm and muggy. I hike a lot..was carrying a 25 lb vest. This hike was hard. I was trying to beat the storms. It is very easy to miss the Mt Prospect trail going up the south slope off the money broom trail. I kept looking for it to branch off to the left after every stream crossing. Thank Godfor the gps. And speaking of going up the south slope of Mt Prospect...damn that was not easy. About 1200-1300 of ascent in about a mile. The thunderstorm did not help. There were no water sources really until Greylock. A couple beautiful views.

Finished in about 5.5 hours and it was a great training hike.

Did this loop with my small dog as an overnight trip, starting with the AT (south) to Mount Prospect, then staying at the Sperry Road campground. Completed the second half including Mount Greylock the next day. Unfortunately there were no views from Greylock due to the very foggy, misty weather, although it did make for a pretty quiet hike. Was definitely made more difficult by having an overnight pack, but I can see this being doable in one day without the pack as long as you begin early and are in really good shape. The trail was well marked the entire way, especially the AT sections.

Summited Northbound on day 5 of an AT section hike. Incredible pine and beech forests and so many wildflowers. The summit was astonishing and we were so happy to have planned to stay at Bascom Lodge to enjoy Greylock for a while.

love this section of the AT

This is a short hike with lots of steep spots scattered throughout (nothing terrible). The trail markings are sad, but the rock features and view at the top are worth it.

This is a moderate loop that takes you over the largest peak in Massachusetts. It includes a Leanto 4 miles from the end for an overnight but this is doable in one day. Recommend starting early in the AM as we didn’t get to camp until about 5pm. Not much for wildlife other than small critters. Fire wood is available in season for leanto sight (not at the one we used). I recommend going in reverse and staying at the Wilbur Clearing leanto. There are serveral fresh water sources as well. This was a great hike and the trails are amazing as well as beautiful waterfall, one of which was right next to our campsite.

2 Guys and a Dog

Great hike. Not quite “easy” as the trail rating suggests.

didn't see ant camp sites but nice hike steep at first we had to set up tent on 12 inches of snow about 5 miles past lake there was no designated camp site or fire pits

Great hike from the AT trailhead near Jug End up to Mt. Everett. steep climb at the beginning then leisurely hike along a ridge with views. Summit is a bit unremarkable, but nice views from the shelter just below. was snowing throughout our hike with no one else on the trail.

Short trip to the top and a bit steep, but very manageable. Can take anywhere from 30 min-1 hr to reach the cobbles, depending on level of fitness and break time. Great view of Cheshire Lake and Mt Greylock. Great spot for sunset too, just bring a light for the trip back down!

Good hike. Not sure why its listed as hard? Ive done this hike probably 20 times (Im local). It is 7+ miles, but not too strenuous. Cheshire to Dalton is a bit harder, because you do much more climbing, including climbing to the cobbles in the beginning. There is also a shelter with a privy about half way.

Nice views from the Pine Cobble junction and Eph's Lookout. Street parking is plentiful along Massachusetts Ave, near the start.

Friday, November 24, 2017

Super pretty in late November. Perfect for a 6 year old and non-hiking 13 year old. Great mix of forest meadow and streams.

Sunday, November 19, 2017

Jogging - it's a beautiful trail to run on . Varied terrain and a great mix of woods and open meadows!

Very easy going section of the AT.. I was able to walk it this fall, very scenic..

Cool spot.

Load More