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Day 5 – Putney to Orange, MA

One Ride Today

  • 61 miles
  • Too Long?  Ask for Head Start Drop-off Service

See the Day 5 Route


Today is a 3 state ride Vermont, New Hampshire and Massachusetts. Leaving camp, we head north, passing the 50’s era Santa’s Land on the way to a river crossing into New Hampshire. It’s not clear if Santa’s land will be open this year, but it still fun to see as is the People Car Company with vintage VWs in various states of repair parked in front.

Once across the river, we have our first rest top in Walpole, NH. Take a few minute to ride into the town center where the original L.A. Burdicks Chocolate Shop and Cafe is located. After a re-fueling you, will head up through the hills to Keene NH. Keene is a neat college town in the Monadnock region and claims to having the largest jack-o-lantern display in the world. They also have lots of quaint shops and places for lunch.

You’ll leave Keene and head for the covered bridges. There are 4 to see before you re-enter Massachusetts. Since the last 20 miles are through lightly populated areas, when you arrive in Winchester, you should stock up on anything you might need. Besides the distillery and tasting room, there is a convenience store in the middle of town.

After the forests and hills of north central Massachusetts, you’ll enter Orange, MA where you can stop at Honest Weight Brewery  (open at 2:30) or continue into the center of town where, if you want, you can eat or kayak before heading to camp an easy mile down the road. Don’t miss Trails Head Outfitters and Miller River Cafe, located in the same building at the intersection of North Main, South Main, East Main and West Main Streets.