22 Best Things to Do in Bennington, VT

Welcome to Bennington, a charming haven nestled in the southwestern corner of Vermont.

From the vibrant autumnal colors that paint the landscapes to the cozy winter evenings spent by the fire, there's always something to look forward to.

Let me guide you through some of the best things to do in Bennington, Vermont.

In this comprehensive guide, we've melded insights from locals and travelers to present you with a mosaic of experiences that define this remarkable place. While we've highlighted some must-visit spots, it's imperative to understand that these recommendations are shaped by personal opinions and experiences.

Spend a Night at The Walloomsac Inn

If you're someone who's in search of a place that combines the charm of history with a dash of the supernatural, look no further than The Walloomsac Inn in Bennington, Vermont.

This 300-year-old building, teeming with tales untold, is a possession of pride for the Pratt family.

As stepping into the inn is akin to stepping back in time.

Every wooden panel, every creaking stair has a story to tell.

One cannot help but be mesmerized by this beautiful, mysterious, giant building standing tall against the test of time.

As a child, I'd sneak up to the inn and press my ear against the walls, hoping to hear the whispers of the past.

Do not be surprised if your stay is extended by a playful ghost named Casper.

This friendly apparition has a knack for keeping you on your toes with his hilarious antics and might just keep you up past your bedtime.

The rooms of The Walloomsac Inn, while somewhat drafty, add to the quaint character of the inn.

Be mindful of your belongings, though, as they might get a taste of Vermont's rain.

From time to time, the inn may close its doors for maintenance, a necessary evil to preserve this historic building.

It's a place that captures the essence of Bennington, a pearl on the string of Vermont's rich history.

Sample the Spirits at Village Garage Distillery

Trust me when I say there's no place like Village Garage Distillery.

From their mouth-watering food to their distinctive cocktails, there's not a single thing that doesn't entice you about this place.

Everything’s just right here.

My personal favorite is their Pineapple Express cocktail - it's as refreshing as a summer breeze and goes down smooth.

The place is a beautiful addition to our town and quickly became my favorite weekend escape.

My partner absolutely relishes their gourmet offerings, and I must say, the food is amazing, except for the pasta that could use a little extra salt.

But no worries there; just ask for a salt shaker, and you're good to go!

But what I love most at Village Garage Distillery is the ambiance.

The chill vibe of the room, the friendly and chill staff, it all adds up to an unforgettable experience.

And if you're lucky, you might even spot a dog there!

My friends and I love the Bonfire - it's the best alcohol we've tried, so much so that we took home a couple of bottles.

And let me tell you, their double chicken and waffles is a game-changer.

Catch a Performance at Oldcastle Theatre Company

Stepping into the Oldcastle Theatre Company, you'll instantly feel the intimate aura of the space.

There's just something incredibly welcoming and pleasant about it that immediately makes you feel at home.

It's not only the physical space though, it's also the staff.

They've always been exceedingly pleasant since my first visit, making the whole experience even more enjoyable.

One of the impressive aspects of Oldcastle Theatre Company is the community troupe.

I've seen them perform several times, and let me tell you, they are brilliant.

Some performances have been truly memorable, showcasing an incredible amount of talent.

It's simply amazing how a small-town theater can harbor such world-class talent.

The theater itself has quite a unique ambiance.

It's a cool space, one that could easily fit in San Francisco's South of Market neighborhood.

This isn't a typical small-town theater you'd expect to find.

It's much more than that.

Visit the Distant Past at the Park-McCullough Historic Governor's Mansion

There's nothing quite like a sunny day spent exploring the expansive grounds of the Park-McCullough Historic Governor's Mansion.

Nestled in the heart of my hometown, this Victorian haven is a jewel I often find myself wandering around, even when the mansion itself isn't open for tours.

A trip to the Park-McCullough isn't just a walk through meticulously preserved history, it's a breath-taking adventure across 200 acres of verdant landscape.

It’s not uncommon for me to spend hours meandering along the trails, relishing the tranquility of the surroundings.

Even though I have seen the mansion from the outside countless times, it never fails to evoke a sense of awe.

One of the best parts about living near Park-McCullough Historic Governor's Mansion is their public cultural events.

These festive gatherings are a treat to be a part of, with the mansion providing a grand backdrop that truly adds a touch of magic to every event.

I have quite often found myself immersed in enchanting music performances, captivating theatre shows, and engaging lectures, all held within this historical gem.

But the real treasure lies inside the mansion. The guided tours are a delightful journey back in time.

The knowledgeable guides meticulously introduce the intricate details of the house, and every tour is a learning experience.

I have often found myself lost in the past, imagining the stories that unfolded within these walls.

Living so close to such a magnificent piece of history is truly a privilege.

I have seen couples say their vows in the Carriage house, families have picnics on the sprawling lawns, and children run around, their laughter echoing through the estate.

It’s a sight that truly warms the heart.

Bring Your Kids to Explore the Wonders of The Dollhouse and Toy Museum of Vermont

You'd think living in the same town as The Dollhouse and Toy Museum of Vermont would dull its charm, but every visit feels as magical as the first.

Stepping into the museum brings back vivid childhood memories of playtimes filled with dolls, toy cars, books, and more.

It's like entering a whimsical world where almost every wall and corner tells a different story.

Being one who appreciates details, I am particularly drawn to the exquisitely detailed and hand-built dollhouses.

Spotting the intricacies in these miniature homes is a delightful game I never tire of.

And it doesn't stop there, they even have an exhibit of tiny museum exhibits talk about a world within a world!

I find that every visit is educational too.

There's a wealth of historical information available that adds depth to the simple joy of admiring the toys.

You could say The Dollhouse and Toy Museum of Vermont is a place where history and fun meet.

And if you have any questions or curiosities, the remarkable woman who runs the place is always there with a friendly smile and a wealth of knowledge.

For those with little ones, this place is a treasure trove.

It's always heartwarming to see my kids so fascinated with the collections.

Plus, there's a little play area with a dollhouse where they can enact their own imaginative stories.

Stroll through History at the Henry Covered Bridge

Every day, I find myself lost in the magic of my hometown.

In particular, the historic charm of the Henry Covered Bridge never fails to captivate me.

Nestled in between the lush hills and meandering streams, the quaint covered bridges are an intrinsic part of our landscape here in Bennington, Vermont.

One can't help but be captivated by the nostalgic allure of the covered bridges.

There are several of them scattered throughout the area, each one a testament to our town's rich history.

Of them all, the Henry Covered Bridge holds a special place in my heart. I've walked its timbers countless times, marveling at its grandeur.

It's always a treat to bring first-time visitors to see it, their expressions mirroring the awe I felt when I first laid eyes on this local treasure.

Henry Covered Bridge is easy to find on Google Maps, and the reward you get from your trip is worth every second of it.

The picturesque surroundings are a perfect backdrop to the bridge - a serene, idyllic setting that seems straight out of a dream.

Just off the beaten path, you'll also encounter a beautiful red house that adds to the area's overall charm.

Bennington itself is a charming town, with its historic downtown and its three covered bridges - including the Henry Covered Bridge.

It's also home to the tallest battle monument in the land, another testament to our town's remarkable history.

Go Trekking at White Rocks

You know, there's something about the early season at White Rocks that just makes the soul sing.

The mud squelching under your boots, the foliage bursting into life, and the promise of the white rocks it's almost too beautiful for words.

One of the best things is the well-worn path that winds its way through the bloom-laden landscape.

It's steep, sure, and after a full day's work, sometimes I only manage a short trek.

But there's nothing quite like pushing your limits and feeling the burn in your muscles from the challenge.

And if you're an early bird like myself, you'll find that the parking at the trailhead is plentiful.

You'll also find a trail map there, ready to guide you on your adventure.

And the blue trail? Oh, it's something else.

It takes you all the way to Bald Mountain, showing off the interior forest views in all their glory.

The streams, the well-marked trail, and the rocky stretches add to the thrill of the hike - it's all there.

But a word of caution: this isn't your leisurely Sunday stroll.

I've hiked long trails before, but nothing quite prepares you for a trek through three feet of snow.

It's a tough hike, no doubt about it.

But with the right preparation - water, snacks, and a good deal of determination - it's an adventure that's well worth the effort.

Peruse the Offerings at Walloomsac Farmers' Market

Every Saturday, I find myself making the familiar drive to the beloved Walloomsac Farmers' Market.

There, amidst the bustling stalls, you'll find me elbow-deep in a bin of the freshest fruits and veggies.

Not to mention, the homemade bread and jams are simply irresistible.

The vendors, always brimming with warmth and friendliness, are one of the highlights of my visit.

Even though not all of them accept credit cards, the market has a clever coin system in place.

I can simply buy coins using my card and use them at any vendor's stall.

So, I never have to worry about carrying cash or leaving without my favorite goodies.

Walloomsac Farmers' Market may be small and the selection limited, but it is a treasure trove for foodies like me.

From meats to coffee, cheese, honey, and syrups - the market is always packed with a variety of offerings.

I never leave without a bag full of fresh produce, delicious baked goods, and an occasional bottle from Spirits of Old Bennington.

The live music adds to the upbeat atmosphere and makes every visit memorable.

I also love exploring the assortment of sprouts, mushrooms, and hemp products available there.

Recently, they've even added CBD oils to their collection. It's these unique finds that keep me coming back week after week.

Walk Down Silk Road Covered Bridge

I've been living on Silk Road for years now, and trust me, there's nothing quite like the Silk Road Covered Bridge, especially on a misty morning.

It's just a short walk from my house, and being near it feels like stepping back in time.

There's a captivating romance to the old wooden structure that's hard to put into words.

The best part is its proximity to the river.

Not many people know this, but you can actually walk down beside the bridge and get near the water.

Silk Road Covered Bridge a favorite spot of mine for a quiet moment or to snap a few photos.

The perspective you get from down there - of the bridge, the water, the surrounding greenery - it's simply breathtaking.

Just a mile or two away, you'll find two more covered bridges - their own little charm add to the picturesque setting of our small town.

And let me tell you, they're a sight to behold, especially when framed by the changing leaves of autumn or the pristine snow of winter.

And not to forget, lighthouses along the coast, covered bridges, and Trout streams inland!

The town is brimming with scenic spots that never fail to enchant locals and tourists alike.

Uncover Hidden Treasures at Fiddlehead at Four Corners

If you're looking for a burst of creativity and a dose of unique art, Fiddlehead at Four Corners is where you need to be.

Nestled in the heart of Bennington, this place has become my artistic haven.

A visit there is always a treat for my senses, with an eclectic mix of art pieces and animation cels that make you appreciate the beauty of creativity.

Navigating through Fiddlehead at Four Corners' website, I stumbled upon an assortment of Bunny Mugs that seemed to beckon me.

I never thought I'd be the one to fall for a mug, but here I am, sipping my morning coffee in a bunny mug and loving every bit of it.

The customer service at Fiddlehead never falls short.

It’s not just about making sales for them; they genuinely care for their customers and their love for art.

Oh, and how can I forget the free shipping across the US? Such a steal, right?

I’ve already hinted strongly to my friends about this, and I can see their interest piqued.

Beyond the purchase, the entire experience at Fiddlehead at Four Corners is noteworthy.

You're allowed to leave your mark in the old bank vault with chalk and observe the store from the top.

It’s a unique blend of art and adventure that you wouldn't want to miss.

Look Back to Revolutionary War History at Bennington Battle Monument

I've always been rather fond of the towering stone obelisk that graces our little town of Bennington.

The Bennington Battle Monument, as it's called, is rather hard to miss, standing at a whopping 306 feet tall.

I've lost count of how many times I've visited this impressive piece of history.

It's just a short walk from my house and has become something of a regular haunt of mine.

Upon my visits, I always make sure to ride the elevator up to the observation deck. You wouldn't believe the view from up there!

You can gaze across the land and see all the way into three different states.

It's quite the sight, believe me.

The monument isn't just all about the view, though. It's a significant piece of our town's history, commemorating a Revolutionary War battle.

You can feel the weight of the past when you're standing in its shadow.

Even more, the Bennington Battle Monument and the park surrounding it have always been beautifully maintained, making it a great spot for a picnic.

And let's not forget the gift shop. It's usually my last stop after a visit to the monument.

It's a treasure trove of quirky memorabilia and historical books, perfect for picking up a little something to remember the day by.

Discover the Hidden Depths of Everett Cave

If you're a fan of adventure and natural wonders, you should definitely visit Everett Cave, a hidden gem tucked away in our town.

It's a short hike, but once you're there, you'll be glad you made the trip.

I usually start my journey from the nearby college, following the trailhead by the field. It's a pleasant walk up the hill leading to the cave trail.

From there, it's a slight detour to the left, and you're right at the entrance of Everett Cave.

Before venturing in, I always wear comfortable clothing and sturdy footwear, as the cave floor can get quite slippery. And, of course, you mustn't forget to bring a strong flashlight or lantern, as the cave is pitch-black inside.

Once at the cave, prepare to encounter a plethora of large spiders and mosquitos at the entrance, but fear not, they won't bother you and only stick around the entrance.

Once you're inside, it's an entirely different world. The cave walls are wet, and the air is cold and damp, a stark contrast to the outside environment.

The floor transitions from rocky to squishy clay, and the sound of water dripping creates a serene atmosphere.

Several chambers are waiting to be explored.

Shine your light around, and you might even spot bats hanging around.

Exploring Everett Cave is truly a unique experience and an excellent adventure for first-time explorers or seasoned spelunkers alike.

As a tight-knit group of 2-4, it's a fantastic way to bond and create unforgettable memories.

The entrance to this trail is conveniently located at Southern Vermont College, next to the gym/stadium.

Be careful if you plan to visit after a rainy day, as the trail may be a bit muddy.

Grab a Pint at Madison Brewing Company Pub & Restaurant

There's something comforting about walking into Madison Brewing Company Pub & Restaurant at the end of a long day.

The hustle and bustle of the day fade away, replaced by the relaxed, family-friendly atmosphere that Madison Brewing is known for.

It's the kind of place where everyone feels at home, and their housemade beers and sodas are just the cherry on top.

One of the signature dishes is their fish and chips.

I remember thinking to myself how surprisingly large the piece of fish was the first time I ordered it.

It was perfectly cooked, flaky on the inside and crispy on the outside.

But Madison Brewing Company Pub & Restaurant isn't just about the good food and drinks.

It's also about the experience.

The dishes are flavorful and leave a lasting impression.

Some might argue that their big plates are not as big as one would hope, but that's a minor complaint compared to the overall dining experience.

I've had times when I regretted not ordering an appetizer to the club with the main course, but the taste of the food makes up for everything.

My favorites, however, are the Fajita Bowl and the Vermont Chicken.

And if you ever get a chance to start your meal with their Brussels Sprouts, don't miss it!

It's a fantastic way to kick off a hearty meal.

Discover the Town's History at Bennington Museum

The first time I walked through the doors of the Bennington Museum, I was blown away by the eclectic collections.

It's not every day you get to see such a diverse range of exhibits, from antiques and musical instruments to tiny sewing machines.

I still remember the thrill of seeing the world's largest Grandma Moses collection for the first time.

Each painting seemed to tell a story, taking me back to a different era.

Now, I make it a point to visit the museum every few months.

The modern gallery may be small in size, but it's packed with thought-provoking pieces that push the boundaries of contemporary art.

The map collection, on the other hand, is like a window to the past, providing a fascinating look at how our understanding of the world has evolved over the centuries.

The museum's grounds are equally impressive. Each time I visit, I make it a point to take a stroll in the botanical garden.

While it's a sight to behold in the summer, there's something incredibly peaceful about seeing it in the quieter months.

Nestled in the woods behind the museum, you'll even find hidden wood plank sculptures.

They have this whimsical charm that never fails to put a smile on my face.

But the Bennington Museum is more than just a place to see beautiful art and interesting artifacts.

It also serves as a repository of local history.

Through its exhibits, I've learned about the significant events and individuals that have shaped not just Bennington but the entire country.

Get Creative at Bennington Potters

One of my favorite pastimes is exploring the local craftsmen's work in my quaint hometown of Bennington, and one of the local treasures is none other than Bennington Potters.

This place is an absolute haven for pottery lovers like myself.

Walking into this beautiful setting, I am always greeted with a wide selection of quality merchandise and handmade stoneware.

It's quite a delight to browse through their variety of pottery, each with different types of glazes. I love how I can mix and match to add a personal touch to my collection.

It's not just pottery at Bennington Potters though; I often find myself drawn to their array of gifting options that include ornaments, seasonal items, table dressing, and even dish towels.

It's fantastic to spot something unique every time I visit.

The experience doesn't stop at the store.

Tucked at the back, there's always a bargain to be found with reduced items.

And for a real treat, I take a peek at the working factory around the back.

It's fascinating to watch craftsmen at work, bringing to life beautiful pieces of stoneware.

A Step Back in Time at Bennington Battlefield State Historic Site

Ever felt the thrill of standing on a spot that played a crucial role in shaping history?

That's exactly what I feel every time I visit the Bennington Battlefield State Historic Site.

This place connects me to the momentous events of 1777 when our forefathers bravely battled the British.

The interpretive signs and trails make the past come alive, making me feel as if I'm a part of the event.

Just a short drive from the grand monument in Bennington, the battlefield site offers stunning views, especially from the top of the hill - a place from where the monument was once visible.

It's a sight that leaves me awestruck every time.

The view of the major battle points, boosted by the helpful displays, breathes life into the tales of bravery and sacrifice.

What really takes my breath away is the spectacular view of Bennington Battlefield State Historic Site in October.

The autumn leaves paint a beautiful tapestry that adds a touch of charm to the historical backdrop.

A pleasant bonus is the always impressive monument.

Though the view from up there may not be as stunning, the small entry fee and the well-maintained facilities make it a must-visit.

And then there's the battlefield, which demands respect and reverence.

The staff here are courteous and knowledgeable, adding depth to the experience.

Book a Tee Time at Mount Anthony Country Club

What a sight. I recall a particular evening at the Mount Anthony Country Club vividly.

The serene sunset, painted with hues of orange and red, was visible through the smoke from the distant Canadian fires - a sad yet beautiful spectacle.

I found myself drawn to the bar, lured by the ambiance's warmth and the friendly staff's familiarity.

My go-to order?

The Heirloom Pork Chop is served with fingerling potatoes alongside a succulent Salmon filet presented on a bed of fresh spring vegetables.

The consistency of their perfect execution never fails to impress.

But it's not just the food and drinks that make this place special.

Mount Anthony Country Club also boasts a stunning golf course, well-kept and in exceptional shape.

Over the years, I've spent countless hours there, absorbed in the panoramic views of the river and the mountains.

However, navigating the back 9 can be a bit tricky due to the less-than-ideal signage.

The greens tend to be fast, unpredictably slanted at times, which makes the game even more challenging.

The undulating fairways often leave your ball either above or below your feet.

It's no easy course, but it sure does keep you on your toes.

The restaurant too, which ranges from fair to good, offers great service. The clubhouse is charming, a nice place to unwind.

It was here where I hosted a Celebration of Life dinner for 17.

The food, as always, was top-notch, and the service was nothing short of outstanding.

Wander around Downtown Bennington Historic District

Every day, I get to experience the charm of living in the Downtown Bennington Historic District.

Rooted in rich history, this place is more than just a district - it's home.

Every morning, I welcome the day with a stroll around the neighborhood, admiring the beautiful historic buildings that hold countless stories of the past.

One of the must-see places here is the stunning monument that many visitors come to see.

It's always a joy to watch their faces light up as they take in the grandeur of the towering structure.

There's always a story to be shared - whether from a new visitor or a long-term resident.

After a morning walk, it's time for breakfast, and there's no better place than one of our local eateries.

The town may not have lots going on, but we take pride in our local restaurants and pubs.

They serve a mix of hearty traditional and exciting contemporary dishes that truly satisfy every palate.

When it's time for lunch, I often head to one of our pizzerias.

Just like one visitor said, we do have delicious pizza!

It's a well-kept secret amongst us locals.

But the food isn't the only thing that's great about our town - it's the people.

The friendly folks at the pizza place, the regulars at the local pub, and the kind strangers who help you when you’re in a pinch.

They all contribute to the warm and welcoming atmosphere of our little town.

In the evenings, I usually wind down with a glass of craft beer from one of our local pubs.

While doing so, I take a moment to appreciate our local products, just like the syrup that visitors often take home as a souvenir.

It's these small things, made with love and care, that make our town special.

And when the rain comes, as it sometimes does, we hunker down and take the opportunity to relax and enjoy indoor activities.

We may even get historic rainfall, but it's just another part of life here in the Downtown Bennington Historic District.

Other Things to Do Nearby

Learn about a Poet's Life at the Robert Frost Stone House Museum

I've spent countless afternoons at the Robert Frost Stone House Museum, each visit more enchanting than the last.

The tranquility of the place seeps into you as you find yourself nestled under a giant shade tree, munching on your lunch while reminiscing about the timeless poetry of Frost.

The charm of this place isn't just in the quaint stone house but also in the picturesque grounds that surround it.

I remember a day when, despite the sign on Google Maps indicating that the museum was closed, the gate invitingly stood ajar.

I strolled in, camera in hand, capturing the sheer beauty of the home and its serene environs.

Oh, I would have loved to have a peek inside the house, but the exterior alone was enough to transport me to the times when Frost himself walked these grounds.

Over the years, Robert Frost Stone House Museum has evolved - it's a beautiful blend of history and modernity.

The ground floor of the house serves as a delightful rural museum, a tribute to Frost's life and work.

On a visit with my young ones, we were captivated by a record player - a charming relic of the past that was a huge hit with the kids.

The museum is also a treasure trove for literature lovers like myself.

I discovered a few unpublished poems of Frost, each one a gem that reinforced my admiration for the poet.

I look forward to seeing more of the house open in the future, revealing more hidden corners of Frost's world.

Stretch Yourself at the Mile-Around Woods

Often, I find myself drawn to the tranquility of the Mile-Around Woods.

There's something marvelously calm about its winding trails, the rustling of leaves underfoot, and the harmonious melody of birdsong above.

This place is more than just a forest; it's a serene retreat nestled in nature’s pockets.

Hiking through these woods is an experience that never gets old.

The terrain is kind, welcoming to both the hardened veterans of trekking and those less accustomed to stretching their legs.

Each winding path offers a new view, a new perspective, and a renewed sense of wonder.

One of the best things about this place is the pure versatility it offers.

It's not just a hiker's paradise, it's also a photographer's dream.

I've seen many a prospective bride and groom choose this place for their engagement photoshoots.

The lush greenery, the falling snow in winter, or the vibrant colors of autumn every season brings a new charm to the woods.

And let us not forget about our four-legged friends.

My dog, Alfie, loves our adventures in the Mile-Around Woods.

Whether it's chasing squirrels or splashing in the creek, the joy on his face is a sight to behold.

There's no better place for a day out with your canine companion.

Have a Retreat at Kimberly Farms

Every year, I find myself being drawn back to Kimberly Farms for an absolute treat.

This little gem in our town has become my favorite place to unwind and reconnect with nature.

I remember my first visit to the farm like it was just yesterday.

It was a sunny day, and I decided to go on a trail ride.

Over the years, my son and I have learned so much about horses.

From grooming to riding, every experience has been an educative one.

Apart from the hands-on experience with horses, the farm also offers hikes, trips to the lake, and arts and crafts.

I noticed a significant change in my son, who is usually very shy. He has opened up, gained confidence, and looks forward to visiting the farm.

If you were to ask me, I would say that Kimberly Farms is not just about horse riding.

It's about building confidence, learning new skills, and most importantly, creating memories.

Indulge in the Cuisines at Kevin's

I've got to tell you, I had high hopes for Kevin's, with its reputation as a long-standing American tavern.

The promise of a cozy dining room brimming with local art was enough to get me through the door.

The thought of savoring a warm French onion soup and biting into a savory roast beef dip was tantalizing.

Upon my visit at Kevin's, I was taken aback by the emptiness of the place on a Wednesday afternoon.

I mean, it's not every day you see such a well-known place without much of a crowd.

The saltiness of the au jus that came with my roast beef dip was a delight for my palette.

The soup?

Well, it was nothing short of delicious.

Final Thoughts

Living in Bennington has been quite an enjoyable experience.

Whether it's the breathtaking beauty of Kimberley Farms, the rich history encapsulated within the walls of the Park-McCullough Historic Governor's Mansion, or the unique offerings of Village Garage Distillery, there's never a dull moment here.

Bennington, with its rich tapestry of history, culture, natural beauty, and friendly community, is truly a hidden gem of Vermont.

It's a town filled with charm and character that leaves an indelible imprint on all who call it home.