Wachusett Mountain Trail Network

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I'd say the nearest significant peak to start building up to Washington would be Monadnock and it isn't too far beyond Wachusett.

I agree. I go to Monadnock often and Pumpelly Trail will likely be our first trial run at a real mountain but it is almost two hours from my house and the person I'm "breaking in" lives about 40 minutes South of me so I was trying to find some closer stuff.
 
You could always wear a heavier pack for your Wachusett hike too. There are some fairly steep parts, they are just shorter sections, 1/4 mile or so.
 
We actually went this past SAT and I enjoyed the trails quite a bit. We parked at Echo Dam Rd (?) lot and went there to High Meadow and Bicentennial up to summit from Pine Link (?) and then over and down the other side, circling around and returning on Jack Frost. Managed to stretch it out to about 5 miles or so. I was coming down with a cold so the light day pack and 50 deg weather was welcome. I will definitely go back and try some other trail combinations. Closest terrain to White Mountains I have around my house.

Wachusett Brewery was pretty cool too, although it is not where I thought it was and I didn't realize they don't have table service. Was absolutely PACKED too! We got there around 2:30PM thinking it would be fairly quiet at off hours and we had to walk around for 5-6 minutes before scooping up two open seats. Fun place though.
 
You must be really close to me. Bigelow hollow is about 20 minutes from where I live. I hike Wachusett fairly frequently. The trails are well marked and it's not a very difficult hike (depending on conditioning) from any direction. I like it as a way to "run" up a mountain. I usually follow the Bolton Pond Trail to start and then there a couple of ways up off of that but it's a nice easy hike to stay in shape with.
 
In the north part of central Mass., the Tully Trail is a great 21-mile loop, which should give you a solid day's exercise.
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I went up and did the Tully Loop yesterday. It had some spectacular areas but it also had a lot of downtime on fire roads, dirt roads and actual roads which was a bit of a bummer. There was also some pretty vague blazing in places and at least two spots where I was following yellow blazes but was not actually on the Tully Trail (at least according to the maps I had with me). It didn't help matters that I researched a bunch of hikes this week so when I started hitting blazes in 3-4 colors I had no clue what color blazes the Tully had. After a 1.5 mile "diversion" only a 1/4 mile down the trail (which led to a beautiful beaver pond which was worth it) I figured out Yellow was my color. Lot of wildlife. Saw 4 huge owls, a beaver, a heron, ducks, crows, vultures, woodpeckers and tons and tons of red and grey squirrels.

I parked at Royalston Falls lot near the little graveyard and went counter clockwise so Tully Mt (the only "real" climb on the map) and the majority of the road walking would be earlier in the day. Thought was the perfect call until I was over 22 miles in and started the last 1.3 miles through the gorge and Royalston Falls. The steep and rough terrain kind of finished me off but thankfully it was spectacular scenery to enjoy while I was huffing and puffing. I wound up getting 24.6 mies out of the day. Definitely got the "solid day's exercise" you advertised. :)
 
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