It's Columbus Day weekend, which means it's the peak of Fall color in New Hampshire. Mount Monadnock provides a 3165 foot vantage point to see the changing leaves of New England and I hike it every Columbus Day.
You'll find a trail map online.
My thoughts on the trails:
Marlboro trail - a favorite of mine, since it is the road less traveled. The upper 1/3 is a bit steeper than most trails and challenging when wet/icy but the views are spectacular and the terrain is a great balance of forest, rock and mud.
Pumpelly trail - this longest trail up the mountain begins in Dublin, NH (near Yankee Magazine headquarters). My wife drops me off at the trail head and I walk the Pumpelly to the top, then Marlboro to the bottom, and run to East Hill Farm, where my family stays each Columbus Day weekend.
Birchtoft trail - a remarkable wooded trail that is a favorite of locals. It's often missing from guidebooks because it's the jewel of the mountain.
White Cross trail/White Dot trail - a well marked, well traveled trail. Good if you like hiking with a group.
Old Toll Road to White Arrow trail- the shortest, easiest trail. Good for families.
There are a few side trails I recommend
Cascade link - beautiful waterfalls and foliage
Marian trail to Great Pasture to Smith Summit - a largely untraveled wilderness path. I play my Japanese flute along these trails and have never seen another hiker
Amphitheater trail - access to a climbing area hidden near the top of the mountain
I've hiked the mountain hundreds of times in all weather conditions at all times of year. It's the 3rd most climbed mountain the world (after Mt. Fuji in Japan and Mount Tai in China) and definitely worth the trip.
You are wearing red!!!
I live in Peterborough, NH and get to enjoy this region everyday and every season - thanks for telling everyone how wonderful it is up here :)
Considering your obvious love of invigorating hikes, I recommend checking out the fabulous Lake Michigan dunes when you are in the area for the HIMSS Midwest conference.
If your schedule permits there are two locations to consider. The first is Sleeping Bear National Lakeshore which is about 3 hours from Grand Rapids. The other is the Silver Lake dune area which is just over an hour northwest of GR. A visit here requires local knowledge about how to get to the dunes out of season - during the summer, you just cross Silver Lake in a boat.
If you've never been and you have time the dunes are an awesome hiking experience.
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