Here are the instructions to the trailheads from I-90 (modified by me to work better):
1. Take MA exit 2 towards US-20, keep left towards US-20 / RT-102
2. Turn left onto US-20 and then right to RT-102
3. Keep straight onto US-7 South and stay on US-7 South
5. Turn right onto SR-41 South (not North)
6. Turn left to stay on SR-41 South and then immediately to the right onto Mt Washington Rd.
7. Continue straight (road name changes to East Street at some point). You pass the Forest Headquarters (on your right), then the road becomes unpaved. Keep going until you see a large parking area and the AMC sign on your left. The first trail (red blazed over Round Mountain and Mt Frissel) starts from the right. A stone state line marker is reported to be here as well although we never saw it
8. Go 1.2 mile past the AMC parking area until you see a small parking area on your right. There is a 2nd small parking area immediately after it that has a metal gate back and to the right (which you cannot see until you stop and look backwards). This is the jeep road that you want to follow. If you hit a lake on the right you went to far. Turn around and go back 2 miles to the parking area.
The road south of the park headquarters (and YMCA) can get a bit confusing. Some say follow East St, others note it changes to West St. The best advice from just returning from there is to "stay on the main road" - it seems quite obvious which choice that is.
Also, the road barricade is not up year-round - it was down when we were there and so we went 3 miles too far to the lake mentioned by Moneal. A sign tells you the state line is 3.3 miles back, so go back.
We spotted the state line monument. The red blaze trail is opposite the "large" (think six cars) parking lot with a gate. The start of the trail offers parking for two cars.
Finally, the actual highpoint (the three-inch pipe) is down from the summit of Mount Frissell. It is in a rocky open area where the view is wonderful. We found it very easy to spot, although some think it is hidden? The trick was to "keep going" down the slope. It is about 500 yards down and around. There were maybe three or four "rocky open overlooks" before you reach the one you want. Go down the steep decline, then round the mountain side.
Please note that you do NOT want to turn right to go to Bish Bash Falls. Keep straight when you come to the intersection with the diminutive church!
Thanks for the information. I have edited the main page accordingly. So Nevada, Connecticut, AND Oklahoma's highpoints are shoulders of higher terrain in other states. I guess a person learns something new everyday.
Actually, Connecticut is the only one. Boundary Peak in Nevada is about 1/4 mile from the California border with a prominence of only 253 feet, but it is a separate sub-peak of Montgomery Peak. Black Mesa, Oklahoma is about 400 yards from the New Mexico border with a prominence of a couple of feet. The whole area appears flat, but it's been surveyed and that spot is higher than the surrounding area. The mesa slowly gets higher in New Mexico, but this "bump" in Oklahoma is the highpoint of the state (marked by a 9-foot monument). Connecticut is the only one where the highpoint is just the slope of a hill.
Mt. Frissell is one of the more remote east coast highpoints. Mt. Riga Rd. and Mt. Washington Rd. are dirt/ gravel roads. When you get to the parking lot, plan on a 50 minute hike from the trailhead to the highpoint. You actually climb to the summit of Mt. Frissell then you hike down from there in a SW direction to actually reach CT's highpoint. The best advice- as offered on this site- "FOLLOW THE RED BLAZES" They will take you to the highpoint.
Mt. Greylock in MA is only about 60 miles way- make it a double!
You're right--a little more than I was expecting. I went in November of 2013 (my 21st high point). It was a cold, rainy day and the "trail" was slick & very ill-defined in some places. The red blazes, however, do get you there. On my way back, however, the fog dropped in and that caused a problem--I couldn't find the exit from that little plateau. To paraphrase (I believe it was) Mark Twain: I wasn't lost, but I was confused for a little while" Nowhere near the highest HP, but one of my most memorable.