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3 Day Itinerary

Mother and two kids at the beach with paddle boards

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Three days is just enough time to fall head over heels in love with The Monadnock Region. Here are some ideas of how to make the most of your time here.  

Day 1:  

Depending on the season, you should take some time to enjoy the outdoors. Here in the winter? Check out either our downhill skiing options or cross-country skiing and snowshoe trails.  

If you’re here during warmer weather, 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.  


If you’re in the mood for something a little more upscale or romantic, check out Granita Enoteca in Keene, The Waterhouse in Peterborough, The Pearl in Peterborough, The Restaurant at Burdick’s in Walpole, or The Chesterfield Inn in Chesterfield.  

When it comes to more casual dining, there’s so much to choose from throughout the region. The Hungry Diner in Walpole, in Keene you have several options, including Luca’s Mediterranean CafeYahso Jamaican Grille, The StageFritz, and many more. Downtown Peterborough also has several options, including Coopers Hill PubHarlow’s Pub, and Twelve Pine.  

For a truly unique dining experience, be sure to check out Mama McDonough’s Irish Pub at the Keene airport. Enjoy a pint and some lunch and maybe you’ll be lucky enough to catch a Black Hawk take a practice landing.  

Be sure to check out the Greater Keene and Peterborough Chamber’s video guide to over 20 restaurants and their best dishes in the area. You’ll definitely end up wanting to extend your stay!

Day 2: Arts and Culture 

Walldogs Mural Tour: Keene, NH 

The “Walldogs” is an internationally renowned organization of sign and mural artists. Every year The Walldogs organize a festival where hundreds of artists descend upon a village or small town to paint a series of murals in a style inspired by wall advertisements from the late 1800’s. In addition to being incredibly impressive, you get to learn about the local history. You can’t help but be moved by the inspiring stories of Dr. Albert Johnston, Jonathan Daniels, Jennie B. Powers, and Catharine Fiske as your stroll downtown Keene.  

While walking, you’ll notice other murals of various styles, like these and my personal favorite, this one by Craig Roach. It’s easy to see why the Monadnock Region is considered New Hampshire’s “cultural corner” by so many.  

For more art, head on over to Peterborough, NH, where you’ll find Trumpet Gallery, the New England Art Exchange, and beautiful shops that sell both home décor and artwork.  

There’s a lot to do here when it comes to arts and culture, and we suggest visiting again during the Monadnock Open Studio Tour or MacDowell Medal Day for the ultimate Monadnock Arts Experience. And for more Arts and Culture recommendations, please click here. .

Day 3: Views and Brews  

We don’t call ourselves the “Monadnock Region” just to laugh at your attempts to pronounce it correctly, you’ll catch of a glimpse of our bare and often snowcapped namesake, Mount Monadnock, from just about every town in the region. While second place is never anyone’s first choice, when number one is Mt. Fuji in Japan, a little bit of pride is inevitable (which is very difficult for New Englanders, except when it comes to The Patriots).  

Hiking Mt. Monadnock will take 3 to 4 hours for most people (unless you’re this guy), and does have some scrambling once you reach the top.  

After all that hiking, you’ve earned yourself an enormous ice cream cone, and Kimball Farm is the place to do it. At first you’ll be like, “Oh no! This is way too much ice cream!” and then you’ll finish it because, holy moly, are you hungry. 

This is also a great day to drink a little and try to casually mention your fitness accomplishment to any stranger who will listen, so maybe grab a pint as the region is home to many excellent breweries

For more ways to fill your day, check out our 5 day itinerary.  

More To Explore

Mother and two kids at the beach with paddle boards

3 Day Itinerary

Three days is just enough time to fall head over heels in love with The Monadnock Region. Here are some ideas of how to make

White circle outline of the monadnock mountain

Visit the Monadnock Region

Here, you can truly thrive, with things to do indoors and out, and endless places to explore, like:

  • Ashuelot River Park
  • Colonial Theatre
  • New England Art Exchange
  • Family farm stores
  • Monadnock Recreational Rail Trial
  • Cheshire Children’s Museum
  • And much, much more.

Explore the possibilities.

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