10 Relaxing Things To Do Near Stamford, Vermont (Bennington County)
If you’re looking for a quiet corner of Vermont that still lets you explore a lot of fun places,
Stamford, Vermont is a great home base. This tiny town in
Bennington County sits right on the Massachusetts border, surrounded by forests, rolling hills, and classic New England charm.
Whether you’re planning a long weekend or passing through on a New England road trip, here are
10 of the best things to do in and around Stamford, VT.
1. Take the Scenic Drive over Stamford Mountain
One of the simplest ways to enjoy the area around Stamford is just to
drive the back roads. Coming into town over
Stamford Mountain (on Vermont Route 8) feels like slipping into another world.
You’ll see:
- Thick forests hugging the roadside
- Classic farmhouses and red barns
- Wide-open views of the Green Mountains
Pull over at a safe turnout and just listen. Most days, you’ll hear more birds and wind than cars.
If you enjoy fall foliage, this drive in late September or early October is incredible. The hills around Stamford glow with orange, red, and gold — it’s like someone turned the saturation all the way up on nature.
2. Hike, Bike, or Snowshoe in the Green Mountain National Forest
Stamford sits close to huge stretches of the
Green Mountain National Forest, giving you easy access to miles of woods and trails. You won’t find tons of big tourist crowds here, which is part of the charm.
You can:
- Hike short forest trails for a mellow walk
- Mountain bike on nearby routes (check local trail maps in season)
- Snowshoe or cross-country ski in winter when the snow piles up
Bring:
- Comfortable hiking shoes
- Bug spray in summer
- Layered clothing (mountain weather changes fast)
If you’re used to busy national parks, the quiet here can surprise you. It’s a great place to unplug, breathe, and reset.
3. Spend a Day in Nearby North Adams, Massachusetts
Just a short drive south from Stamford, across the state line, you’ll find
North Adams, MA. It’s an easy “day in town” when you’re staying in rural Vermont.
Top things to do in North Adams:
- MASS MoCA (Massachusetts Museum of Contemporary Art) – one of the largest contemporary art museums in the USA, set in old brick factory buildings.
- Local breweries and coffee shops – perfect for a relaxed afternoon.
- Downtown murals and small shops – great for a casual stroll.
If you’re traveling with family or a group, MASS MoCA is nice because you can wander at your own pace. Some exhibits are huge and interactive, and you don’t need to be an “art expert” to enjoy them.
4. Drive the Famous Mohawk Trail
From Stamford, you’re only a short hop away from the
Mohawk Trail, one of New England’s classic scenic byways, running through the mountains of western Massachusetts.
Why it’s worth the trip:
- Big, sweeping mountain views
- Roadside overlooks for photos
- Quaint small towns and antique shops along the way
The Mohawk Trail is especially popular in the fall, but even in summer it’s a beautiful ride. If you like Sunday drives, this one will stick in your memory.
Tip: Fill your gas tank in North Adams or Bennington before you head out, and bring snacks so you can take your time and stop wherever you like.
5. Explore Downtown Bennington, Vermont
About 30–40 minutes northwest of Stamford,
Bennington is the county’s lively hub and an easy half-day trip.
Here you can:
- Walk the historic downtown with its brick buildings and local shops
- Visit Bennington Battle Monument, a massive stone obelisk with sweeping views
- Check out local cafés, bakeries, and pubs
The
Bennington Battle Monument stands over 300 feet tall, and on a clear day, you can see into New York and Massachusetts. If you like a bit of Revolutionary War history mixed in with your scenery, this stop is ideal.
6. Chase Covered Bridges Around Bennington County
New England and covered bridges go hand in hand, and Bennington County has some of the prettiest ones. While Stamford itself is more about forests and backroads, a short drive opens up several classic bridges.
Some favorites near Bennington:
- Silk Road Covered Bridge
- Paper Mill Village Bridge
- Henry Covered Bridge
These are perfect for:
- Photo stops
- Quiet walks by the water
- Short breaks on a driving loop
If you’re road-tripping through Vermont, you can easily turn this into a fun “covered bridge hunt” and see how many you can find in one day.
7. Ski, Ride, or Hike at Nearby Jiminy Peak or Mount Snow
If you visit Stamford in winter, you’re within driving distance of several ski areas. Even in summer and fall, many of these mountains run lifts or offer hiking and mountain biking.
Popular options within a reasonable drive:
- Jiminy Peak (MA) – skiing, snowboarding, and a fun mountain coaster in warmer months.
- Mount Snow (VT) – a larger resort with lots of trails and a busy ski town vibe.
You don’t have to be a hardcore skier to enjoy these places. Many families:
- Take lessons on the beginner slopes
- Ride the lift just for the views
- Hang out in the base lodge with hot chocolate
From quiet, woodsy Stamford, it’s nice to dip into a busy resort area for a day, then return to your peaceful rental at night.
8. Enjoy a Quiet Cabin Stay Under the Stars
One of the best “activities” near Stamford is actually doing almost nothing at all.
Because of its rural location and low light pollution, Stamford is an amazing place to:
- Rent a cabin or farmhouse
- Sit around a fire pit on cool evenings
- Stargaze on clear nights
If you’re coming from a city or suburb, the night sky here can feel shocking. On moonless nights, you might see more stars than you’ve noticed in years.
Bring:
- A warm jacket, even in summer (nights can be cool in the hills)
- A simple stargazing app on your phone
- Marshmallows and a campfire-safe setup, where permitted
This is the kind of place where you actually hear the crickets, the creek, and sometimes nothing at all. It’s a gentle reminder to slow down.
9. Visit Local Farms and Roadside Stands (Seasonal)
Bennington County and the surrounding areas are full of
small farms, especially once you branch out from Stamford into nearby towns.
Keep an eye out for:
- Roadside farm stands with fresh vegetables and flowers
- Maple syrup sold directly from local producers
- Seasonal apples, pumpkins, and berries
In late summer and fall, you may find:
- Pick-your-own orchards
- Country stores with local cheeses and jams
Checking out a farm stand can turn a simple drive from Stamford into a fun little food tour. It’s also a nice way to support the local community.
10. Take a Scenic Loop to Williamstown & the Berkshires
From Stamford, you’re also close to the pretty college town of
Williamstown, Massachusetts, at the edge of the Berkshires. It makes a great loop drive:
- Start in Stamford, VT
- Head south toward North Adams
- Continue west or east into the Berkshires or up to Williamstown
- Circle back to Stamford via quiet country roads
In Williamstown, you can:
- Walk through a classic New England college campus (Williams College)
- Visit The Clark Art Institute for art and scenic grounds
- Enjoy small-town restaurants and cafés
It’s a great mix: rural Vermont mornings, artsy Berkshires afternoons, and peaceful nights back in Stamford.
Planning Your Trip to Stamford, Vermont
Here are a few quick tips to make travel around Stamford smoother:
- Getting there: You’ll almost certainly want a car. Stamford is quiet and rural, with no major public transit.
- Best time to visit:
- Fall – for foliage and scenic drives
- Summer – for hiking, lakes, and long evenings
- Winter – for nearby skiing and cozy cabin stays
- What to expect: No big box stores or nightlife in Stamford itself; think country roads, dark skies, and lots of quiet.
If you’re craving crowds, head to Bennington or North Adams for the day. If you’re craving calm, Stamford itself delivers.
Have You Been to Stamford, VT or Bennington County?
Have you driven over Stamford Mountain, visited Bennington’s covered bridges, or spent time in the Green Mountain National Forest?
- Which spots did you like best?
- Do you have a favorite scenic drive, hike, or small town café in the area?
Share your experiences, tips, or questions in the comments below. Your ideas can help other travelers plan their own peaceful Vermont getaway.
And if you found this guide to
things to do near Stamford, Vermont helpful, please
share it with a friend who loves quiet backroads, mountain views, and small-town New England charm.
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