Recommendations for "warm up" hikes around NW Conn

Okay, I'm ready to relinquish winter and start my hiking season. Of course, I haven't really hiked in a good 4 or 5 years, so I'll have to spend some time warming up this season. I've done Bear and Race Mountains before near Salisbury, and the hike to Hublein Tower. Any other suggestions for day hikes in the area that 1) aren't longer than 5-6 miles round trip, 2) allow dogs on the trail, and 3) can be done by someone who isn't exactly in peak physical condition. We did the trail to Hublein Tower from the reservoir a couple weeks ago and realized we would need some warming up before we attempted any overnight trips for sure. Any suggestions?
Thanks a bunch!

Those that live in your area will post some good hikes.

Glad to read you are looking forward to hiking!

NW CT is my hiking stomping grounds! I typically hike Bear and Race 2-3 times a year. I'm not sure how you did them, but here are some suggestions:

• Undermountain --> AT --> Bear (up-and-back or down AT to Sages --> Paradise --> Under Mountain)
• Lion's Head to Bear via AT (rather long up-and-back [~8 miles?] but with a long flat section in the middle)
• Race Brook Falls to Race (up-and-back)
• South Taconic Trail to Alander (up-and-back)
• Prospect Mountain/Rand's View - AT (flat and easy)

It's a great area. Here are some images:

Alander Mountain - August 19, 2001
Mount Everett and Mount Race - December 10, 2000
Race Brook Falls - November 12, 2000
Prospect Mountain / Rand's View - November 5, 2000
Tri-State Loop - October 14/15, 2000
Bear Mountain - October 8, 2000
More Alander Mountain - September 19, 1999

For Trip reports, see:

Bear & Round Mountains - October 12, 2001
Mount Washington State Forest / Riga Plateau - December 10, 2000
Mount Bear & Sages Ravine - October 24, 2000
Race Brook Falls/Mount Race - October 24, 1999

Alander is a must. This site has some great info on Alander. Here's a link to get a map of the area. More info on Mount Race & Mount Everett from GORP. Info from Backpacker.com. This truly is a wonderful area. Hope this helps!

Besides those; Everett via Elbow Trail behind berkshire school, Jug End, it's steep but good practice if heading up North later in the year.
Brace, Breadloaf & Pine Bend Loop off of Route 7. Higby near I-91 & Castle Crag.

In Central Mass, Tom, Holyoke's Toby also offer some early season warm ups.

Geat ideas! We've done Bear up & back and via Paradise & Undermountain Tail before. I've also done Race from the parking area on the main road. A few years back in college my husband (boyfriend then) and I took a Backpacking course. We did a long 2 night backpacking trip--unfortunately, the exact details are fuzzy now. I know we had a short hike in on Friday night to the Tom Leonard Shelter. The next day the group went over that mountain (we had to head back down & go into town to replace a broken hip belt buckle). We met them on the other side and continued on the trail to Everett, which was a long day of hiking for a group of mostly novices. Not only that, we lost a deaf student on the trip, and my husband and I were trying to help the teacher (we were the only ones who brought cell phones then--which turned out to be quite useful under the circumstances as it enabled us to keep in contact with the teacher even though he was miles behind us at one point). In any case, the student never showed up into camp, so the next day the local fire station came up and hauled us down the mountain. Guess they didn't want him to lose any more students. Fortunately they found the student--he went back to the Tom Leonard Shelter and spent the night there. In any case, I haven't done any backpacking since that experience...
I'll have to pull out the maps I just got and plan some trips. Thanks for the ideas!