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5-day Itineraries

Autumn trees near a lake

5 Day Itinerary

Have five days to spend in the Monadnock Region? Lucky you! Let us help you make the most of your time here.   Our first recommendation is to consider splitting up your stay, maybe a few nights at a local farm or a cozy inn, and then spend a few nights in of one of our more bustling downtown areas, like Keene or Peterborough.   Day 1: Getting Settled   After a few hours of driving (the Monadnock Region is 2 hours from Boston and 3 from New York), it’s always nice to stretch those legs. The region is home to all kinds of trails, from casual walks to more intense climbs. For your first day, we recommend an easy stroll, maybe on the Cheshire Rail Trail a nice walk around Cranberry Bog in Peterborough or one of the shorter trails of the Harris Center in Hancock.   Now that the car is parked and you’ve gotten in some steps, how about a great cup of coffee and maybe a sweet treat? Brewbakers, Prime Roast Coffee, Fire Dog Bakery, Kristin’s Cafe, Burdick’s Chocolate Shop and Cafe, Twelve Pine, Barn & Thistle all have something to help you get you through until dinner.

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View from kayak in a Fitzwilliam new Kayak/Canoe rental company

Splish Splash

Water defines New Hampshire’s Monadnock Region—literally! The Connecticut River runs along our western border, as it winds its way into Massachusetts and beyond. (You may

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A couple walking in Downtown Keene, NH

Keene, NH

Keene, New Hampshire is a relatively small city in the southwestern corner of the state. With three colleges, a collegiate summer baseball team, and a

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Girl checking out at Antique shop

Shopping

There are three hubs for shopping in the Monadnock Region; Peterborough and Wilton, both in Hillsborough County, and Keene in Cheshire County. Scattered throughout the

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Sleigh Rides

Looking for a relaxing yet thrilling adventure for the winter? Why not go on a sleigh ride! Read about the most popular places below and

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Skating outdoors on a frozen pond

Wintertime Family Fun

As the winter months approach, everyone is looking forward to the fun activities of the season like skating and sledding. Keep reading to know the

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A collection of pumpkins and gourds viewed from above

Pumpkin Picking

Does it get more fall than picking out that perfect pumpkin? Whether your a pumpkin pie baker or creating a front door scene themed “undertaker,”

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Big smiles on the Rail Trail, Keene

Family Fun

The Monadnock Region is a great place to spend time with the family. We have outdoor activities available year-round, live entertainment options, and cultural experiences

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Farm Stays

Looking for excellent accommodations, wide open spaces, a country breakfast, crisp fresh air, and maybe even a rooster’s crow? We’ve got you covered. From fully

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Night Skiing at Crotched Mountain

Downhill Skiing

The Monadnock Region has two downhill skiing options within its borders and a few other mountains located close by.   Within the Monadnock Region:  

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