Mount Frissell, The CT High-Point & The NY/CT/MA Tri-Point *RECOMMENDED*

99 Mt Washington Rd
Salisbury, CT 06068

Website: https://www.alltrails.com/trail/us/massachusetts/mount-frissell-and-brace-mountain-loop-trail

Activities: Hiking, Leaf Peeping

Last Visit: October, 2020

Notes: There are a few parking spaces along the road by the trail-head which is right at the CT/MA border. A larger lot is located about a 1.25mi south on Mt Washington Rd near the trailhead should you wish to do this hike in reverse.

I have wanted to do this hike for years:
•Three peaks (Round Mountain, Mount Frissell and Brace Mountain)…
•In three different States…
•Plus the highest point in Connecticut…
•As well as the New York / Connecticut / Massachusetts Tri-Point (where all three State borders touch)…
•All in one 5.25 mile hike!

The first mile is the most difficult as you ascend Round Mountain (in CT) and then Mount Frissell (in MA), both of which afford beautiful views along the way. After you reach the summit of Mount Frissell you cross back into Connecticut at the CT Highpoint. A short trip down the trail is the NY/CT/MA Tri-Point where you will find a stone obelisk that marks the spot the three borders converge (although they left Connecticut off the marker for some reason!?!).

From Frissell’s summit it is a much easier hike along a ridge to the top of Brace Mountain in New York. The summit is very open with absolutely amazing vistas. After that it’s an easy and pretty downhill trail through the woods back into Connecticut ending at Mt Washington Rd. The last 1.25 mi is a dull but quick stroll along the road.

Recommended stop: If you came up Rt. 22 in NY, drop by McEnroe Organic Farm in Millerton for an excellent meal in their beer garden. We ate there and watched the sun set – perfect end to a wonderful adventure. http://www.mcenroeorganicfarm.com/

Macedonia Brook State Park

159 Macedonia Brook Road
Kent, CT 06757

Website: https://portal.ct.gov/DEEP/State-Parks/Parks/Macedonia-Brook-State-Park

Activities: Hiking, Leaf Peeping

Last Visit: October, 2020

Notes: Please take note of the Rock Scramble.

An amazing place for a fall hike with great views of the surrounding countryside. We hiked nearly the entire Blue Loop; parking at the Camp Office, we took the Yellow trail and then hiked the Blue in a counter-clockwise direction – it was about 6.7 miles.

The park is close to Kent, CT – a very pretty little New England Countryside town that is now filled with trendy (and expensive) galleries and eateries. We were going to stop for some coffee and pastries on the way out but the whole town was absolutely swarming with people! So take note if you plan on visiting with your hike – it gets very crowded on pleasant fall days.

Rock Scramble: If you go to the AllTrails review of this hike, you will see warnings of a difficult rock scramble section of the loop hike. These are not exaggerated. There is a very steep and rocky elevation change to be negotiated, including two 4-5 foot ledges that must be scaled up. Our pupper is a “big, strong, sturdy girl” – but she still needed two big boosts at those sections and ended up with a scraped up leg (I carry a human & doggy first aid kit in my day pack and recommend you do the same). If you have a smaller dog that can be lifted up or down, then it will be no problem. But bigger dogs will need to be OK with getting pushed/pulled over the ledges. It’s not impossible, but it’s difficult. Going up seems to be easier for the dogs than going down. You can avoid the scramble all together by doing an “out-and-back” hike to the summit of Cobble Mountain along the “Macedonia Ridge Trail.” Frankly, the Ridge Trail was the most scenic part of the park other than the the tip of Hilltop Pond (which can be reached by car for a quick scenic stop if you wish).