Keene, New Hampshire: 10 Best Short Road Trips Nearby

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10 Easy Road Trips From Keene, NH: Fun Things To Do Just Outside Cheshire County

If you live in or around Keene, New Hampshire, you probably love that small-town feel and the beautiful Monadnock Region. But sometimes, you just want to hop in the car, grab a coffee, and see something new. The good news? There are a bunch of simple, out-of-county day trips from Keene that are perfect for a Saturday drive, a date day, or a low-key family adventure. Below, you’ll find 10 short road trips, all outside Cheshire County, in these nearby areas:
  • Hillsborough County, NH
  • Sullivan County, NH
  • Franklin County, MA
  • Worcester County, MA
  • Windham County, VT
Each trip includes approximate drive times from Keene and ideas for what to do when you get there.

1. Manchester, NH – City Vibes, River Walks & Foodie Finds (Hillsborough County)

Approx. drive: About 1 hour 10 minutes east of Keene Manchester is the largest city in New Hampshire, but it still feels manageable and friendly. It’s a nice change of pace from small-town life. Things to do in Manchester:
  • Stroll along the Merrimack River — Walk the riverfront paths, watch the water, and check out the old mill buildings.
  • Visit the Currier Museum of Art — A small but impressive museum with classic and modern pieces. Great for a rainy day.
  • Explore Elm Street — Coffee shops, restaurants, and local bars line the main drag. Perfect for an easy lunch or dinner stop.
  • Catch a game or show — Depending on the season, you might find a minor league hockey game or a concert.
If you’ve been craving more food options or a bit of nightlife, this is one of the best Keene to Manchester day trips you can take.

2. Nashua, NH – Shopping, Dining & Riverfront Trails (Hillsborough County)

Approx. drive: Around 1 hour 15 minutes southeast of Keene Nashua has a nice mix of big-box shopping and a charming downtown. It’s ideal if you want to run errands and still enjoy a little exploring. Things to do in Nashua:
  • Walk Mine Falls Park — Miles of wooded trails near the Nashua River. You can walk, bike, or just sit by the water.
  • Shop at Daniel Webster Highway — Big stores, chain restaurants, and everything you “don’t have back home.”
  • Stroll downtown Nashua — Brick buildings, local shops, and casual eats make it a laid-back spot to wander.
If you’ve ever thought, “I wish I could get all my shopping done in one trip,” this is your road trip.

3. Milford & Wilton, NH – Small-Town Charm & Classic New England (Hillsborough County)

Approx. drive: About 55 minutes east of Keene Looking for a slower, classic New England feel? Milford and nearby Wilton make an easy, low-stress day trip. Things to do around Milford & Wilton:
  • Milford Oval — The town center has a small green, shops, and local restaurants. It’s simple, but that’s the charm.
  • Local diners & bakeries — Grab breakfast or a slice of pie at a no-frills spot where everyone seems to know each other.
  • Drive the back roads — The rural roads around Wilton are perfect for a fall foliage drive.
This trip feels like visiting your friend’s hometown in a movie—familiar, easy, and cozy.

4. Claremont, NH – Mill Town History & River Views (Sullivan County)

Approx. drive: About 1 hour north of Keene Claremont sits along the Sugar River and has that old mill town feel that New England does so well. Things to do in Claremont:
  • Walk the historic mill district — Old brick buildings, a river, and bridges that are great for photos.
  • Explore the downtown area — Small shops and local spots to grab lunch or a coffee.
  • Enjoy Sugar River views — On a nice day, just walking along the water is relaxing.
If you like quiet places with a bit of history and character, this is a good day trip from Keene that doesn’t feel too “touristy.”

5. Newport, NH – Simple Main Street & Lake Country Gateway (Sullivan County)

Approx. drive: Around 1 hour 10 minutes north of Keene Newport is a small town that often flies under the radar, but it’s a great starting point if you want to feel like you’ve “gotten away” without driving hours. Things to do in Newport:
  • Walk the town common — The central green and surrounding buildings give you that classic New England postcard look.
  • Check out local shops — Small businesses, antique spots, and simple cafes make for an easy day.
  • Use it as a base — From here, it’s easy to continue north into lake and mountain country if you want a longer drive.
If you love relaxed, no-rush days, Newport might surprise you in a good way.

6. Brattleboro, VT – Artsy, Funky & Right Across the River (Windham County, VT)

Approx. drive: About 35–40 minutes west of Keene Even though it’s in Vermont, Brattleboro often feels like part of Keene’s extended neighborhood. It’s one of the most popular short road trips from Keene. Things to do in Brattleboro:
  • Explore downtown Brattleboro — Bookstores, record shops, and art galleries line Main Street.
  • Check out local food and beer — Cafes, breweries, and farm-to-table spots are common here.
  • Walk along the Connecticut River — Enjoy the water views and look back across toward New Hampshire.
If Keene is your hometown-style hub, Brattleboro is your artsy, slightly quirky cousin.

7. Mount Snow & Dover Area – Mountain Escape (Windham County, VT)

Approx. drive: Around 1 hour 15–1 hour 30 minutes northwest of Keene Want a mountain fix without heading all the way to the White Mountains? The Mount Snow area in southern Vermont is a handy option. Things to do around Mount Snow:
  • Hit the slopes in winter — Skiing, snowboarding, and snowshoeing are the big draws in the colder months.
  • Try summer activities — Hiking, mountain biking, and scenic chairlift rides are common in the off-season.
  • Relax in Dover — Small-town restaurants and inns give you that cozy mountain village feel.
This is one of the best weekend getaway ideas from Keene if you want a little adventure without a long drive.

8. Greenfield, MA – Parks, Trails & Quiet Back Roads (Franklin County, MA)

Approx. drive: About 1 hour southwest of Keene Greenfield is a small city in western Massachusetts with a mix of outdoor access and low-key downtown spots. Things to do in Greenfield:
  • Poet’s Seat Tower — A short hike or drive up to a stone tower with views over town and the hills beyond.
  • Greenfield Energy Park & local trails — Simple walking areas for a casual stroll.
  • Explore downtown — Coffee shops, local restaurants, and a friendly, laid-back vibe.
If you like Greenfield, it’s also easy to pair it with other Franklin County towns like Deerfield or Turners Falls for a full day out.

9. Amherst, MA – College Town Energy & Culture (Franklin County, MA)

Approx. drive: Around 1 hour 15 minutes southwest of Keene Want more bookstores, coffee shops, and people-watching? Amherst is a classic New England college town, thanks to the nearby universities. Things to do in Amherst:
  • Walk around town — Sidewalks, shops, and student energy make the center of Amherst lively almost year-round.
  • Visit museums and campuses — Depending on the season, check out campus art museums or just stroll through the college grounds.
  • Try new restaurants — You’ll find more international and vegetarian options than many small towns offer.
This is a solid trip if you’re craving a bit of culture, diversity, and that “college town buzz.”

10. Worcester, MA – Big City Without the Overwhelm (Worcester County, MA)

Approx. drive: About 1 hour 30 minutes south of Keene Worcester (pronounced “WUSS-ter” or “WOO-ster”) is a mid-size city that’s grown a lot in recent years. It has more to do than a small town, but it’s not as intense as Boston. Things to do in Worcester:
  • Hang out in the Canal District — A revived area with restaurants, bars, and sometimes events.
  • Visit local museums and parks — Depending on your interests, you can find art, history, and green space.
  • Sample the food scene — Worcester’s restaurant options keep expanding, from casual eats to more creative spots.
If you’ve been thinking about exploring a new city that’s still driveable in a day, this is a strong pick.

Tips for Planning Your Keene Road Trips

To make these short road trips from Keene, NH even more enjoyable, keep a few simple tips in mind:
  • Check the season: Some activities (like skiing or foliage drives) are best at certain times of year.
  • Bring snacks and water: Especially if you’re exploring smaller towns with fewer options.
  • Layer your clothing: New England weather can change fast, even on a short drive.
  • Leave a little unplanned time: The best road trip memories often come from the places you find by accident.

Where Will You Go Next From Keene?

One of the best things about living in or near Keene is how many different places you can reach in about an hour or so—mountains, rivers, small towns, and mid-size cities are all within easy driving distance. So, which of these 10 out-of-county day trips are you going to try first?
  • Are you more into artsy towns like Brattleboro and Amherst?
  • Do you prefer simple, quiet escapes like Newport or Milford?
  • Or are you ready for city energy in Manchester, Nashua, or Worcester?
Now it’s your turn: Have you taken any fun road trips from Keene that others should know about? Did I miss one of your favorite spots in Franklin, Worcester, Hillsborough, Sullivan, or Windham Counties? Share your ideas and experiences in the comments so fellow New Hampshire travelers can discover new places too. And if you found this guide helpful, please share it with friends and family who live in Keene or are planning a trip to the area. A simple share might inspire someone’s next great day trip.
Location: Georgetown, IN, USA

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