Keene, New Hampshire: 10 Best Things To Do Nearby

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10 Fun Things To Do In and Around Keene, New Hampshire

If you’re looking for a small New England city with charm, cool shops, and easy access to nature, Keene, New Hampshire, in Cheshire County, is a great pick. Keene is big enough to have great food, live events, and a classic downtown, but small enough that you can walk almost everywhere. Plus, you’re just a short drive from mountains, lakes, covered bridges, and old mill towns. Whether you’re planning a weekend getaway from Boston, a fall foliage road trip, or just wondering what to do near Keene, this guide walks you through 10 awesome things to do in and around Keene, NH.

1. Stroll Downtown Keene and Central Square

Start right in the heart of town: Downtown Keene and Central Square. This area is what makes Keene feel like a classic New England movie set. (In fact, some movies *have* been filmed here.) You’ll find:
  • Brick storefronts with local shops and cafés
  • The landmark United Church of Christ with its tall white steeple
  • Plenty of benches to sit and people-watch
  • Seasonal decorations and events in the square
Walk up and down Main Street and duck into:
  • Bookstores with creaky wooden floors
  • Local bakeries and coffee shops
  • Gift shops with New Hampshire-made products
On a nice day, grab a coffee, sit by the square, and just watch life in a small New England city roll by. It’s simple, but it’s also one of the best things to do in Keene.

2. Hike (or Drive Close To) Mount Monadnock

Just under an hour from Keene, you’ll find one of the most climbed mountains in the world: Mount Monadnock. Technically it’s in Jaffrey and Dublin, but it’s a classic go-to for anyone staying in Keene. Why it’s worth the trip:
  • Great views: On a clear day, you can see into Massachusetts and Vermont.
  • Multiple trails: From more direct, steeper routes to slightly longer but easier ones.
  • Perfect fall hike: The foliage from the summit is stunning.
The mountain is a little over 3,100 feet, so it’s not a casual stroll. Wear good shoes, bring water, and check the weather. If you’re not into long hikes, you can still drive the back roads around Monadnock and enjoy the mountain views from below. Thinking of visiting in fall? Try to go early in the day—parking lots fill up fast.

3. Walk or Bike the Cheshire Rail Trail

If you like quiet paths and easy walks, you’ll love the Cheshire Rail Trail. This old railroad line has been turned into a long, mostly flat trail that runs right through Keene and out into the surrounding countryside. From town, you can hop on the trail for:
  • A short walk to stretch your legs
  • A relaxed bike ride
  • A peaceful run away from traffic
Sections of the trail take you through:
  • Wooded areas
  • Over old bridges
  • Past streams and wetlands
If you’re visiting with kids or just want something low-key, this is one of the easiest outdoor things to do near Keene. You can do as much or as little of the trail as you feel like.

4. Visit the Horatio Colony Museum and Nature Preserve

For a mix of history and nature, check out the Horatio Colony Museum & Nature Preserve. In town, the museum is set in an old 1806 Federal-style home. Inside, you’ll find:
  • Antique furniture
  • Art and decorative pieces
  • Stories about one of Keene’s notable families
Just a short drive away, the Horatio Colony Nature Preserve gives you:
  • Miles of hiking trails
  • Quiet forest paths
  • Viewpoints over the hills of Cheshire County
If you enjoy slow travel—wandering through an old house, then walking in the woods—this combo is a perfect way to spend half a day in Keene.

5. Enjoy Events and Concerts at Keene State College and The Colonial Theatre

Keene may be small, but it has a lively arts scene, thanks in part to Keene State College and the historic Colonial Theatre. Keene State College often hosts:
  • Student and faculty concerts
  • Theater productions
  • Public lectures and film showings
In downtown Keene, the Colonial Theatre is a beautifully restored venue that brings in:
  • Live music and touring bands
  • Comedy shows
  • Classic and independent films
If you’re planning a weekend trip to Keene, it’s worth checking the schedule ahead of time. Seeing a show here adds a nice “night out” feel to your stay.

6. Explore Covered Bridges Around Cheshire County

New Hampshire is famous for its covered bridges, and Cheshire County has some great ones within an easy drive of Keene. A fun half-day drive could include:
  • Thompson Covered Bridge in West Swanzey
  • Cresson Covered Bridge (also in Swanzey)
  • Other small bridges tucked along side roads and rivers
These old wooden bridges feel like walking into a postcard. Many cross quiet rivers with forested banks—perfect for photos, especially in the fall. Tip: Bring a simple picnic or grab takeout from Keene and make it a covered bridge road trip. Stop, take photos, walk across, and enjoy the slow pace.

7. Tour Wineries, Breweries, and Cider Places Near Keene

If you enjoy local drinks, the Keene area has a growing number of small breweries, wineries, and cider makers. Around Keene and Cheshire County, you can find:
  • Craft breweries with cozy taprooms
  • Country wineries with tastings and views
  • Cider spots that celebrate New England apples
Choices change over time, but you’ll often find spots that focus on:
  • Small-batch beers
  • Seasonal flavors (pumpkin ales, apple ciders, etc.)
  • Relaxed, local vibes instead of big crowds
If you’re traveling with friends or as a couple, this can be a fun late-afternoon activity after hiking or exploring downtown Keene. Just be sure you have a safe ride if you’re tasting more than one place.

8. Go Apple Picking and Visit Local Farms

Fall in New Hampshire means one thing: apple season. Near Keene, you’ll find local farms and orchards where you can:
  • Pick your own apples
  • Try fresh cider and cider donuts
  • Buy maple syrup, jams, and other local treats
Even outside of fall, many farms in Cheshire County offer:
  • Farm stands with fresh produce
  • Flowers and plants in spring and summer
  • Christmas trees and wreaths in winter
If you’re visiting New Hampshire with kids, apple picking near Keene is a must-do. It’s one of those simple, old-fashioned activities that still feels special.

9. Explore Nearby Towns: Peterborough, Walpole, and More

One of the best things about staying in Keene is how easy it is to explore nearby small towns in southern New Hampshire. Within about 30–45 minutes, you can reach places like:
  • Peterborough: A charming town with artsy shops, galleries, and a pretty downtown.
  • Walpole: Known for its hilltop views and small village center—plus great chocolate and ice cream nearby.
  • Harrisville (a bit farther): A historic mill village with a lake and red-brick buildings.
These towns give you a feel for the wider Monadnock Region—rolling hills, old mills, church steeples, and winding back roads. If you enjoy slow drives and “let’s see where this road goes” days, basing yourself in Keene works really well.

10. Enjoy Seasonal Festivals and Markets

Keene and the surrounding area host different seasonal events throughout the year, which can really change the feel of your visit. Depending on when you go, you might find:
  • Fall festivals celebrating foliage, apples, and pumpkins
  • Holiday markets and winter events with lights and decorations
  • Summer concerts in parks or on the common
  • Farmers markets with local produce, baked goods, and crafts
These events are a great way to meet locals and get a real sense of community life in Keene, NH. If you like to plan ahead, check local calendars or the city/tourism websites before your trip.

Planning Your Keene, New Hampshire Getaway

Keene is a friendly, walkable base for exploring southern New Hampshire and the wider Monadnock Region. In just a couple of days, you can:
  • Wander downtown and Central Square
  • Hike (or at least admire) Mount Monadnock
  • Walk or bike the Cheshire Rail Trail
  • Visit covered bridges and local farms
  • Catch a show or concert at night
Whether you’re here for fall foliage, a quiet winter weekend, or a summer road trip, there are plenty of things to do in and around Keene without feeling rushed.

What Would You Add to This Keene, NH List?

Have you been to Keene or elsewhere in Cheshire County?
  • What was your favorite thing to do near Keene?
  • Did you discover a great café, hike, or hidden spot?
Share your tips and experiences in the comments—they might help someone else plan their own trip to Keene, New Hampshire. And if you found this guide helpful, please share it with a friend who loves small New England towns, fall road trips, or weekend getaways.
Location: Georgetown, IN, USA

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