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5 Day Itinerary

The NH Monadnock Thrive Guide


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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.  

And for a pre-dinner cool down, how about a dip at Ware’s Grove Beach in Chesterfield? It’s the ideal spot to catch a sunset.

Chances are, you’ll be on your feet a lot while here, and you may discover a love of paddleboarding, kayaking, cycling, or snowshoeing (depending on the season, of course!). Pick up some new footwear or rent some outdoor gear to make the most of your stay. EMS in Peterborough has both your gear and rental needs, or Ted’s Shoe and Sport in Keene, Sam’s in North Swanzey also have the latest in active footwear and clothing for sale.  


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.  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.  Learn more about the mountain here.

If you’re here in the winter, perhaps swap out a visit to Monadnock for our one of our Downhill Skiing or Cross-country Skiing options.

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.  

Day 4: Shopping and Wellness  

You’ve spent a lot of time in nature and the arts and my goodness, you’ve earned a few hours to find that perfect new sweater, antique, or book to complete your collection. The Monadnock Region is home to some excellent shopping, and you can read about it all here.  

After lunch, why not treat yourself to a massage? Deep RootsMudita, and Everglow Wellness in Keene all offer massage. For a full spa experience, check out European Estethics in Peterborough where you can get a facial, a massage, and even your make-up done.  

Day 5: Morning Cycle, Evening Show  

We have all kinds of terrain for your preferred style of cycling, from the easy trails of our rail trail systems (Monadnock Recreational Trail, Cheshire Rail Trail, Ashuelot Rail Trail (pronounced ash-wee-let) to mountain biking at Drummer Hill.  

We also have two bike parks, both with areas for beginners (even little, little ones using balance bikes) and areas for those experienced enough to flip and jump. These bike parks are well maintained and both near two excellent playgrounds, making them each a great way to spend an entire day with the family  

Keene Bike Park: Keene, NH 

Located in Wheelock Park, this park has little hills for those just learning and a more complex course for those looking to catch some air. It’s quieter in the early morning if you are looking to just practice, and come later to see some real action (the beginner trails are off to the side and available all day). Wheelock is an awesome park with multiple playgrounds (in the shade!) and other activities too.   

Throughout the Region there are a number of live music venues, the largest being The Colonial in Downtown Keene. We’ll list some of the larger venues here and for a complete list click here: https://discovermonadnock.com/welcome-nhs-cultural-corner/live-performance/  

The Colonial Performing Arts Center, Keene, NH 

The Colonial, the largest local theater with 800 seats, has been a staple of the community since opening its doors in 1924 when Vaudeville was the hottest ticket in town. In 2022, a major renovation was completed, and the stage and shows are better than ever. From traveling Broadway productions to acts like Scotty McCreery, Lucinda Willams, Jazz from Lincoln Center to family shows like The New York Theater Ballet’s Nutcracker, there is truly something for everyone.  

Nova Arts @Brewbakers, Keene, NH 

Nova Arts is the live event space arm of the restaurant/cafe Brewbakers. It’s a beautifully designed space that offers a highly curated selection of live performances throughout the week. From Traditional Irish sessions to established artists to Yo La Tengo to up and coming artists, you’ll find something here to move you, no doubt about it. Be sure to check out their annual musical festival in May, “The Thing in the Spring.”  

Park Theatre: Jaffrey NH 

With 333 seats in their newly renovated auditorium, The Park Theatre is a great place to catch an independent film, a live show, or something more academic, like a panel discussion featuring experts addressing topics from racial injustice to climate change. 

More To Explore

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

Bartender serving champagne to two besties

Dining in the Monadnock Region

Whether you spend the day on the water, hitting the trails, or searching for antiques, you’re going to work up an appetite on your journey

The NH Monadnock Thrive Guide


Our friends at Yankee Magazine have put together a special online visitor guide to all that’s great about our region. As a bonus, you’ll get a copy of our monthly eNewsletter.

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