The Best Monadnock Region Outdoor Adventures

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The Monadnock Region of New Hampshire is chock full of outdoor adventures for everyone. When outdoor enthusiasts think of adventure activities in New Hampshire they often look to the White Mountains or Lake Winnipesaukee. However, the area surrounding Mount Monadnock is an awesome outdoor playground too. There are hiking trail networks, gorgeous lakes and rivers, rail trails, and covered bridges. Follow the New Hampshire motto and live free!

Where is the Monadnock Region?

The Monadnock Region is in the southwest corner of New Hampshire. If you took a compass and inscribed a 25-mile circle around Mount Monadnock you will have the Monadnock Region. There are 40 charming New England villages known for their picturesque beauty. Don’t miss Hancock, a tiny whitewashed settlement of historic buildings.

The only city is Keene, a laid back college town with great restaurants and murals of their most famous citizens. The region is less than a tank of gas away from all the eastern population centers. This place has a road trip written all over it.

The Ashuelot River flows throughout the region. Ashuelot is the name give by the Sokoki Native American tribe for their land. It means the “land between places”. The Abenaki name for Grand Monadnock means “bare or smooth mountain.”

Where to Stay in the Monadnock Region

Splitting a trip to the Monadnock Region into two parts allows for a chance to see and do many adventures. I based in Keene in the southern part of the region for half my trip. Then I stayed in Acworth to enjoy more northern outdoor adventures in the region. Staying in two places made easy access each day to outdoor activities, but you can certainly just base in one area and visit the whole region because things are so close. I found the most lovely places to stay in each area so I’m glad I didn’t have to choose.

Elm City Carriage Barn

This charming bed and breakfast inn is located on shade tree-lined Main Street across from Keene State College. It’s a pleasant walk to town to enjoy the diverse restaurants and brewpubs of Keene. The history of the inn is shown in its hewn wood beams and whimsical folk art wall painting.

Elm City Carriage Barn is a twofer–a luxurious room and the sweetest innkeeper you will ever meet. Personable inn owner Will is totally committed to making your stay pleasant and comfortable.

The guest house offers a deluxe continental breakfast but since I stayed during the pandemic, a gift card to a local breakfast place substituted. I’m sorry I missed Will’s coffee which I hear is legendary.

The best deal at the Elm City Carriage Barn is the humbly named Room 5. The unkept secret of a 2 bedroom, 2 bath apartment is a spectacular find for traveling families. It’s spacious with a granite countertop full kitchen, brand new wood floors, and a jacuzzi tub. A perfect place to base for adventures in the Monadnock Region.

Captain Woodbury Guesthouse

The picturesque common of the charming town of Acworth is next to the Captain Woodbury Guesthouse. You can sit out on the back deck of the inn and watch the setting sun bake the meringue colored church to a perfect golden hue. Serenity is the theme you will find here.

Innkeepers Dennis and Sally have set up a gorgeous, welcoming environment for all kinds of travelers. There are spacious bed and breakfast rooms with their own sitting areas in the main house. An endless breakfast featuring produce from the magnificent vegetable gardens and eggs from the very polite chickens in the backyard is a highlight.

There are also seasonal options for staying here. Several campsites with all the camping amenities are on the property. A great camping benefit is the use of the common room at the back of the house for cooking or watching TV on a rainy afternoon.

The best deal at the Captain Woodbury Guesthouse is the Back Shed Room. You have an outdoor hot shower and a very clean privy, but also have access to the main house sitting rooms and the delectable breakfast. It’s so simple and quiet, a great place for a retreat. The room is only available from May to October so don’t miss it.

Outdoor Adventures of the Monadnock Region

Here are hiking and biking options for the Monadnock Region. My most recent visit was in the summer so many warm weather options are detailed. Don’t forget that fall foliage in New Hampshire makes it a destination in itself. And cross country skiing areas and alpine ski resorts are sprinkled throughout the region.

Mount Monadnock Hiking

The outdoor adventure centerpiece of the Monadnock Region is 3,165-ft. Mount Monadnock, the bare top mountain rising conspicuously above the rest of the area. I have always heard that Mount Monadnock was the second most hiked peak in the world, after Mt. Fuji in Japan. Whether this is New England legend I don’t know. But when I’m on the summit with a few hundred new friends, I tend to believe it.

Even with all the foot traffic, Mount Monadnock is a worthwhile and reasonable climb for most hikers. The views across most of New England from the top are unparalleled.

It is possible to avoid the crowds on Monadnock, but you must hike strategically. Here are hiking strategy suggestions:

• Hike early or late. Sunrise on the mountain is worth the early alarm clock. I’ve camped nearby and got an alpine start for a chance to pretty much have the mountain to myself. In the summer, the extra light means dinner on top with few people. Just bring your headlamp for the end of the hike.
• Use a lesser-used trail. The most popular trails, the White Dot and the White Cross, start at Monadnock State Park headquarters. Try a trail on the other side of the mountain from here for a quieter hike. I like the Marlboro or Dublin Trails.
• Hike in the winter. With the right equipment and good judgment, a winter climb of Monadnock in the winter is awesome.

Winter Hiking Recommended Equipment

1. Hiking Poles. I really like my Black Diamond Trail Trekking Poles. They are lightweight, adjustable for all conditions, and super durable. For more economical poles, try ALPS or Leki. But if you are really going to use poles consistently, invest in the Black Diamond poles.
2. Microspikes. I’ve tried many different microspikes and the Kahtoola Microspikes are the best for icy hikes. Mount Monadnock is a sheet of ice sometimes, but these microspikes will make you feel like Spiderman on the ice.
3. Day Park with food and water. Osprey makes excellent day packs. For day hiking, a 24-liter up to a 36-liter daypack is best. The number after the brand name will tell you the size of the pack. For winter hiking I use a 36-liter pack for extra layers. The Osprey Stratos packs are excellent.
4. Insulated water bottle—Hydro Flask will keep liquids hot on a winter hike. A sip of tea on the summit of a mountain is divine.
5. Headlamp. Day hikers should always carry a headlamp in case you are caught after dark. I’ve always used Petzl headlamps for their excellent lumination and battery life. My favorite is the Petzl Tikka headlamp.

For more information about winter hiking, jump over to my post on

Proven Winter Hiking Tips

Pisgah State Park

Did you know that Pisgah State Park is the largest state park in New Hampshire? It doesn’t really come off as your traditional state park with the manicured entry and the ranger booth. Instead, access to Pisgah is at 6 trailhead parking lots surrounding the park. Your only entrance fee is a promise to keep this unspoiled park pristine when you leave.

And since it’s an unstaffed park you are on your own to be a safe and responsible visitor. Here’s my experience of being trapped while visiting on a windy day. Call 911 when this happens and some nice firefighters will show up to let you out.

Pisgah has 7 ponds, each surrounded by granite boulders that make swimming access easy even if you don’t jump off them. To find a good swimming spot, enter from the trailhead on Route 63 on the west side of the park. Hike in on the Kilburn Road for .7 miles to Kilburn pond, a popular place to swim in Pisgah. A 6-mile loop hike around Kilburn and several other ponds forks off either way. This hike is mainly through the woods passing glacial erratic boulders along the way.

To find the areas of old-growth forest in Pisgah explore the trails near North Round pond. Views of Mount Monadnock and the Ashuelot watershed can be had by climbing the Pisgah Ridge Trail.

The area surrounding Mount Monadnock is an awesome outdoor playground. There are hiking trail networks, gorgeous lakes and rivers, rail trails, and covered bridges. Share on X

Biking in the Monadnock Region

Backroads biking is superb in the Monadnock Region. While traffic teems up I-91 on the Vermont side of the Connecticut River, the roads on the New Hampshire side are a secluded mecca for cyclists.

There are several rail trails to ride to explore the area. The 21-mile Ashuelot Rail Trail travels over old trestle bridges past farms and abandoned mills that used to be the lifeblood of the area. Woolen mills depended on dams on the Ashuelot River for power.

The Cheshire Trail trail is 32 miles in length and intersects the Ashuelot Rail Trail. Both bike paths have some rough spots so they are not recommended for road bikes.

Bike the Bridges tour

A wonderful bike route to see picture-postcard New Hampshire is the Bike the Bridges tour. This 12-mile loop starts at the Cresson Bridge near Swanzy Station. There is parking here and a sign showing the route. You can also bike a short way here from Keene to start the route.

You will end up seeing 4 different covered bridges, cute small towns, and spectacular countryside. The route travels part of the time on the rail trail with the rest on very quiet country roads. Halfway along you will discover Swanzy Lake. Bring some lunch fixings to picnic on the shore of Swanzy Lake. There are plenty of farm stands on the route in the summer to buy goodies. Restaurants are more scarce.

Bears Den Natural Area

This natural area in Gilsum is all about the rocks. Boulders, mica, potholes! Cliff and caves! Oh, my!

There are big boulders with crevices to explore at the end of the half-mile trail. Rumor has it there is a 200-foot cave there but I looked in a lot of dens and found neither a big cave nor bears. Perhaps you will find the cave or come face to face with a bear. But probably not the bear!

The trail in Bears Den is like a sea of glitter from mica scattered on the ground. The area is known for its abandoned mica and feldspar mines. Therefore, you will see crystals of all shapes and sizes wherever you look.

About 5-10 minutes into the hike, there will be potholes on the left before the trail descends. While it might be a humble display of glacial potholes, you will still scratch your head trying to figure out how they got there. Potholes tend to form from swirling water carving out the characteristic curves. So how did this happen high on a hill?

Follow the orange dot marked trail to get to the bear dens. After exploring this area, look for an unmarked trail heading uphill. This approach trail for local rock climbers to get to a climbing crag will bring you up to a beautiful cliff with exceptional views. Have lunch on a house-sized rock with a view of the Monadnock Region splendor.

Bears Den is located on Route 10 in Gilsum. Trust your GPS or you’ll miss the sign hiding in an indistinct parking area. If you are there at the end of July, pick some wild blueberries.

Gilsum Gorge

The Ashuelot River through Gilsum Gorge is on all the lists of secret swim spots in New Hampshire. Even if you don’t want to swim, it’s worth a visit for its natural beauty. Located downstream from the historic Stone Arch Bridge, you will find it by following the many trails into the gorge. Here there are jumping boulders and cool clear water. The river cascading through the arch is mesmerizing.

Pitcher Mountain

In the summer, this destination on Route 123 near Stoddard is all about the blueberries with a mountain hike involved. Talk about hiking rewards.

You can make a loop by hiking up the Monadnock-Sunapee Greenway trail to the fire tower. Blueberry bushes line the trail as you approach the bald summit. (Pitcher Mt. is a monadnock too).

Enjoy the views from the fire tower. Mount Monadnock is prominent to the south. On a clear day, the whole panorama gives views of the Green Mountains in Vermont and the White Mountains to the north.

Continue the hike by going north through the blueberry fields. You can pick your own wild blueberries with a small donation that goes to maintaining this wonderful resource. After you have picked your fill, follow the trail down through the woods to a dirt road. Bear left to return to the parking lot.

The whole scene is like the children’s book Blueberries for Sal. If you have never read this book to a kid, put it on your bucket list.

Blueberry season in the Monadnock Region runs from roughly the end of July through August. It’s still a wonderful hike with sweeping views even outside of blueberry season.

Wrap up of Outdoor Adventures of the Monadnock Region

This is a small sampling of outdoor adventures in the Monadnock Region. The area is also blessed with several long-distance hiking trails. The Ashuelot River has many sections to paddle. I’ve enjoyed whitewater boating on the Ash during the spring. There are also flatwater sections to float in the summer. I found a group of recreational kayakers putting in below the Cresson covered bridge.

It’s amazing to find a rare pocket of wilderness in southern New Hampshire so Pisgah State Park is a precious gem for exploring. It’s possible to bike on some of the rail trails up into mountain bike trails through Pisgah.

All in all, there are so many outdoor adventures to string together. Take a week or a long weekend to base in the Monadnock Region to get them all in.

If you want to combine a visit to the Monadnock region with nearby Western Massachusetts outdoor adventures, take a look at this post on 10 Awesome Outdoor Pocket Adventures in Western Massachusetts.

Disclaimer: I was a guest at the inns mentioned. I was not compensated or asked to write a positive review. All opinions are from my honest experience.

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