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Historic buildings and museums, a walkable downtown, and oodles of New England charm… Have you ever visited the small, but bustling town of Bennington in the southwest corner of Vermont? Not only is Bennington a historic gem, but it’s also incredibly beautiful in ever season.
Oh, and did I mention that Bennington, Vermont is also my hometown?
Beautiful places in Vermont are pretty easy to come by, and the natural beauty in and around Bennington is what made me fall in love with it more than 14 years ago. In fact, I’ve lived in Bennington longer than anywhere else, and I can’t imagine calling any other place home, no matter how much I love to galivant around the country.
Located just three and a half hours from New York City, three hours from Boston, and an hour from Albany, Bennington is the gateway to Vermont, and well worth a visit no matter where you’re coming from. I may be biased, but I think Bennington is one of the loveliest places to visit in all of Vermont.
Whether you’re looking for a girlfriend getaway, a romantic weekend for two, or a family vacation, Bennington, Vermont will not disappoint! The first thing you need to plan your trip to Bennington is a little inspiration, so I’m sharing seven of the most beautiful spots in town to encourage you to drop everything and plan your visit.
The photos in this post are mostly taken from my Instagram account, which is very “Vermonty,” with a few other lovely places sprinkled throughout for good measure. Ready to explore the oh-so-charming and welcoming town of Bennington, VT? Here are some amazingly beautiful places in my hometown, as well as some reasons that I think you should make a visit.
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How to Get to Bennington, VT
Bennington is located in the southwest corner of Vermont, basically right on the border of both New York to the west and Massachusetts to the south. It’s a pretty easy drive from anywhere in the northeast, which is why we recommend it as a great road-trip destination.
Pro Travel Tip: Give yourself 2-3 days to explore all of Bennington, especially if you love the outdoors. If you want to explore some of the surrounding towns like Wilmington or Manchester, plan for at least 4 days.
If you’re coming from out of state, the closest airport is Albany International, which is an easy one-hour drive. Again, maybe it’s a biased opinion, but I adore flying in and out of the Albany Airport and always consider myself very fortunate that it is so close.
Why You Should Drop Everything and Visit Bennington, VT
With just about 14,000 people, Bennington is a small town surrounded by rolling hills, the Green Mountains, farms, and forests. By Vermont standards, it’s actually a big town – the sixth-largest in the state! Bennington is the county seat and a hub of activity in Southwestern Vermont.
If you love the outdoors, you will definitely fall in love with Bennington, where you can hike, paddle, fish, and mountain bike without leaving town. Here are a few reasons why you have to visit Bennington, Vermont, as well as some beautiful spots that you won’t want to miss.
Bennington is Gorgeous in Just About Every Season
I say just about because I’m not terribly fond of mud season. I’ve lost whole boots to muddy quagmires in the month of March, and I’ve known others that have lost cars! Luckily, mud season in Vermont is short, lasting through March, and as long as we keep climate change at bay, I think I can handle it.
Lucky for us all of us, mud season goes hand-in-hand with maple sugaring season, so I guess that’s reason enough to cut it some slack!
When you think of a typical Vermont vacation, you are likely thinking about fall and winter. Autumn in Vermont is known for the jaw-dropping foliage that blankets the forests and mountains in colorful displays. And winter, of course, is famous for skiing and snowboarding in the Green Mountains.
I love Vermont in every season, but there’s nowhere I’d rather be than here in Bennington in the summer. We’ve got swimming holes. Creemee stands. Fireflies. Mountain Sunsets. Farmers’ markets. I just wish summer was longer!
7 Beautiful Places to Visit in and around Bennington, VT
Have I convinced you to book your next vacation in Bennington yet? Well, let me sweeten the pot by sharing some of my favorite spots with you. The following spots are heavy on natural beauty, with a bit of history and pure New England charm thrown in for good measure. I’ll admit that I’m an outdoor-lovin’ gal, so my favorite places reflect that.
Whether you’re just passing through Bennington, or are making it your destination, these are spots you won’t want to miss.
The Old First Church in Old Bennington, VT
Judging by the number of tour buses and photographers I’ve seen at the Old First Church over the years, I think it might just be the most photographed building in New England. The Old First Church is such a lovely place to explore, even if you’re not visiting during leaf-peeping season.
If you do find yourself here in any season, be sure to check out the rest of Old Bennington. It’s like stepping back in time. You can even take a self-guided walking tour around town.
The Old First Church is the first gathered church in Vermont. Although the church that stands there now isn’t the original, it’s been around since 1805.
Sunday worship takes place at 10 am during the summer months and 11 am during the rest of the year. You can also pop in for a tour with a local volunteer when the church is open. The Old First Church is open for visitors every weekend from Memorial Day to July 1st, and daily from July 1st to the end of Vermont’s fall foliage season.
While you’re there, be sure to visit the grave of one of our most famous residents, Robert Frost, who is buried in the beautiful old graveyard between the Old First Church and the Bennington Museum, which is another great stop for lovers of both art and history.
The Bennington Battle Monument
While you’re in Old Bennington, you won’t want to miss a tour of the Bennington Monument, which you can see from the Old First Church. At 306 feet, the Bennington Monument is the tallest building in the state. It’s the most popular of all Vermont state historic sites, and the views from the top are spectacular.
The Bennington Monument was completed in 1889 to commemorate the Battle of Bennington, which took place on August 16, 1777. In that famous battle, Brigadier General John Stark and 1,400 New Hampshire men, defeated two detachments of the British army, who were seeking to capture a store of weapons and food maintained where the monument now stands.
Although the battle is called the Battle of Bennington, it actually took place about 10 miles west in Walloomsac, New York.
Visitors can ride to the top in an elevator from mid-April until October 31st from 9 am to 5 pm. Learn all about Bennington’s place in the Revolutionary War and be sure to have a picnic on the lawn.
This is also one of my favorite spots for dog walking on a summer evening.
The Robert Frost House in Shaftsbury, Vermont
I’ve already mentioned that Mr. Frost is buried in Bennington, but he lived for a period in a little stone house in Shaftsbury, the next town over. The Robert Frost Stone House Museum is run by Bennington College and is open for visitors from Friday through Sunday from 10 am – 4 pm.
While visiting this literary landmark, be sure to walk the grounds, and perhaps the beautiful nature trail that starts behind the barn and heads out to Lake Paran in North Bennington.
The Robert Frost Trail is 2 miles, one way, and meanders through the woods and along stone walls. It’s easy to envision Robert Frost walking these same country trails before heading home to pen some of his most famous works.
Lake Shaftsbury State Park, Shaftsbury, VT
While you’re in Shaftsbury checking out the Robert Frost House, please take a walk around the lake at Lake Shaftsbury State Park. This is a small, but gorgeous park, with a beach for swimming, great bird watching, and a really nice trail.
As of 2019, dogs are welcome on the trails, which is a new and welcome development for us! The hike around the lake is just about a mile – it meanders through a gorgeous wetland, onto a ridge, and over two nice walking bridges. Lake Shaftsbury is also a great place to throw a line in and catch some trout.
If you go during the (Memorial Day – the second Monday in October), the cost is $4 for adults and $2 for kids. During the off-season, you can park outside the gate and walk in. There are kayaks, canoes, and paddle boats available for rent in the summer.
Woodford State Park in Woodford, VT
Another gem of a place, just10 miles outside of Bennington, in the Green Mountains east of town is Woodford State Park. This is a quiet park with several nature trails, a small lake, and kayak/canoe rentals.
If you’re itching to go camping, Woodford State Park is where you want to do it. Sites are very private and some are located directly on the water. The lake at Woodford State Park is cold, even in summer, but it’s such a paradise! In my opinion, this is one of the most beautiful places in all of Vermont.
The Appalachian Trail in Bennington, VT
The famous long-distance trail runs across route 9 between Bennington and Woodford, and there’s a parking area right off the road for hikers. The Appalachian Trail runs north and south, but we prefer hiking south to Harmon Hill, for the beautiful views of Bennington.
The hike up to Harmon Hill starts off really steep for a good, heart pounding climb. After a mile or so, it levels off and travels through a high meadow, finally opening up to awesome views. The hike totals around 3 miles, with a total elevation gain of 1,000 feet.
If you hike north on the Appalachian Trail, you will head up Maple Hill in the Glastenbury Wilderness. This is another steep hike, but without the view at the end. Still, it’s a lovely hike through the woods and worth checking out.
Park McCullough House in North Bennington, VT
This historic, Victorian-era house was built in 1864 and is considered one of the finest and best-preserved Victorian mansions in New England. You can visit this beauty, the working farm behind it, and the lovely, Mile-Around-Woods hiking trail all in one afternoon. This is one of my favorite places to walk and take pictures, and we always bring visitors from out-of-state here for picnics.
Park McCullough House is open for tours on weekends from summer until the end of fall foliage season. Admission is $15 per person. Special events are also hosted throughout the summer and include concerts, movies, wine tastings, and free yoga in the garden.
As usual, this post focuses almost entirely on outdoor excursions, but there are also cool museums, lots of shopping, and good restaurants in Bennington. If you decide to come to Vermont for a visit, feel free to contact me. I’d love to show you around!
Resources for Exploring Bennington, VT
What to do – The Bennington Chamber of Commerce has a great events page, plus lots of ideas for places to explore while you’re in the area. Vermont Begins Here has a great blog that I often contribute to.
Where to eat – Want some ideas for where to get some yummy grub? Bennington has lots of choices, but here’s what I’d recommend: For bread and baked goods head to Bakkerij Krijnen on East Main Street. Eat breakfast at the Blue Benn Diner, lunch at Madison Brewing Company, and dinner at either Allegro on Main Street, or Pangaea in North Bennington.
Where to stay – We love the Four Chimneys Inn for a splurge and the Harwood Hill Motel for a budget option. If you want to camp, we highly recommend Woodford State Park.
Finally, there are some really great rental deals on Airbnb. We have friends who just listed a really cute house in North Bennington, within walking distance of Park McCullough. It’s three-bedrooms for under $100 a night.
Want to read more about vacationing in Vermont? Check out these posts or jump right to our Vermont Vacation Guide for Outdoor Lovers:
61 comments
When does the foliage season end in Vermont?
Still lots of color out there. The red maples are almost done, but the oaks, birches, and beeches are still really colorful and will be for another week at least.
It looks like the same people paid you like they paid other outlets to promote the same things and places.
Hi Michael,
This post is not sponsored and I was not paid. I live here and these are the places that I love to visit over and over again!
So pretty! I lived in Bennington for a few years when I was little while my mom was attending SVC. I went back for the first time about a year ago for a foliage drive and to take my kids to the monument. I forget how cute Bennington was and can’t wait to go back for another visit.
It is such a cute town, Regan. I’ve been here for 13 years and I still love walking around with my camera.
Tara, Thanks for such an informative post on your lovely hometown! My four daughters and I are spending time in Vermont this August and we made plans for an afternoon in Bennington. For sure we’ll need to pick up some baked goods for the road so thanks for the recommendation. All the best, Gwen
Thank for the tips on places to see in Bennington! We will be making our first trip to the NE from Louisiana in about 3 weeks and we are very excited! We will be staying at Four Chimney Inn!
Anita, you will love the Four Chimneys! It’s a great place to stay and within walking distance to Old Bennington. It’s the perfect time of year to visit too!
If you drop by the Four Corners in downtown Bennington, you’ll see street art in the intersection – a compass and piano keys. Google for more information as it hit AP news back in May 2017. After a harsh winter, it’s in need of a touch up but still great to see.
Hi Tara, thank you so much for sharing these beautiful photos, s gad will be returning to Bennington, and the wonders of Nature there and in the surrounding area!…….Great Work!!
hi tara, thanks for the great information on Bennington. My family and I (husband and 3 teenagers) are doing our first road trip to new england states from detroit. we are so excited and will make sure we check out your 7 places. our plan is to go to burlington, acadia and then down the coast to make stops at coastal towns and finish in boston. any suggestions you can give us on places not to miss and quaint towns to stay in would be so appreciated. we have been saving up and will probably be our only time as family there. i traveled with my parents when i was a teenager to this part of country and will always remember it as my best trip..want that for my kids. thank you tara!!!
Hi Stacey –
I have lots of tips that I can give you! I am just finishing up a road trip of my own and will be back home in Bennington later today. After Burlington, I’m guessing you’ll drive through the Green and then the White Mountains. I would suggest stopping in Stowe/Waterbury. If you’re set up to camp, you can stay in Little River State Park. In New Hampshire, I’d definitely check out Franconia Notch and if you want you can drive to the top of Mt. Washington. Acadia is awesome, but I’d also check out Boothbay Harbor as you’re heading south toward Boston. We lived there for many years, and it’s a really cute town. Have fun!
Hi Tara,
Allen McCullough here. Thanks for boosting beautiful Bennington and the Park McCullough House!
I am on the board there and we appreciate referrals. Might I send you a picture of the house to post ?
Thanks again
Allen, A photo of the house would be fabulous – just let me know who I should credit. I have taken many over the years, but I can’t quite get the lighting right.
I’ve recently relocated to Bennington from New York City and it has been quite the change! I have to thank you for creating this post, seeing all of these beautiful places makes me excited to explore my new home!
That’s awesome, Erica! Welcome to the neighborhood! You will find lots and lots to explore, but these places are some of my favorites.
Don’t forget Southern Vermont College!!! I graduated from there in 95 and still take my kids up there every time we’re in town.
You’re right, Kathy. I love exploring SVC and Mount Anthony. Have you been to the cave?
Tara, I’m one of the volunteers who welcomes visitors at the Old First Church in Bennington ( 7 days a week, late June through October, 10 am – 4 pm). It is an amazingly beautiful church; we love sharing it.
It is the first gathered church in Vermont, but the 2nd church building, built in 1805. The first one was in the green in front. There’s a stone there in commemoration.
Rockingham and Windsor have older church buildings . younger congregations!
Thanks so much for clarifying that, Jane! What a beautiful place to volunteer.
We will be in Vermont later this year. I am about to hit google maps and see if we can spend a night or two at Bennington. If we do I am going to track down every spot you have photographed – they all look so lovely.
Lyn,
I’m so glad you’re going to check out Bennington! Feel free to contact me if you want recommendations for restaurants or lodging.
Tara,
Thank you for your post. We will be driving from Philadelphia to Woodstock, Stowe, and NH. Would you recommend some hidden gems that are not touristy? Any great cheese farms on the way? Towns not to miss? Lakes? Farm to table restaurants where locals are eating. We are planning to start with Woodstock on October 10th. Hope it’s not too late for foliage this year. I Will greatly appreciate your advice.
Thanks a lot!
Alla
Hi Alla –
It shouldn’t be too late for leaf-peeping during your visit, although the colors are changing a bit earlier than normal this year. Woodstock and Stowe are both so beautiful, although they are the two most popular places to visit during October, so it will be busy. In Woodstock, definitely check out Sugarbush Farm, but call first because I’m not sure how they are handling public visits during COVID. Quechee Gorge, while touristy, is a must-visit, as is Billings Farm and Museum. For dinner in Woodstock, we like The Prince & The Pauper. The Ottauquechee River Trail is a new 3-mile walking trail that is supposed to be lovely, but I haven’t checked it out yet.
From Woodstock, I’d recommend hopping on Route 100 and driving north to Stowe that way, especially if you are heading up on a weekday. Stop at Moss Glen Falls, Warren Falls, and Blueberry Lake in Warren. The Stowe area is very touristy, but if you get on the back roads, you will be treated to some great views. Dining recommendation – Hen of the Wood in Waterbury, but definitely make reservations. I’ll email you this as well. Have a great vacation!
i haven’t been to VT in a while. Great reminders of why I like it! and thanks for joining #wkendtravelinspiration
Picture postcard gorgeous! I had no idea Vermont was so beautiful. You made the right choice!
I love these pictures! Vermont is such a beautiful place!
I believe that we see more when we are visitors to other areas than the place we live and that makes it harder to write about. I was raised outside of Chicago but, sadly, never really experienced the city.
Exactly, Betty. I feel the same way. I’ve been trying to be a tourist in my town for the past few months. It’s been so much fun!
Oh wow, such gorgeous scenery! I wish I had the wherewithal to deal with the climate but I can’t even stand Missouri weather, lol. I do love Vermont, though. My grandpa (or should I say, one of my grandmother’s many husbands!) was born there upstate and it’s just always so lovely.
Also, your pic in the sidebar is so cute! The color of that scarf is great with your skin, sooo pretty!
Thanks Nancy! I’m usually the one behind the camera, so this is one of just a few photos I could find of myself.
We are quickly falling in love with Vermont! We’ll be north of you this fall, but now we’re thinking maybe we should venture south, too! Your hometown is gorgeous! Thanks for showing us! #WeekendWanderlust
How beautiful is your hometown! I have been to Vermont a few times but never really visited Bennington, looks a beautiful place! Lovely photos.
xx, Kusum | http://www.sveeteskapes.com
I need to go to Vermont! Your pictures and descriptions are beautiful. I am greatly interested in hiking more of the Appalachian Trail (only hiked some of it in GA and PA), but now I have even more reasons to visit Vermont. I adore Robert Frost. Thanks for the fabulous information!
I want to visit Vermont so bad! Gorgeous photos.
Vermont certainly is a gorgeous state! Love, love, love your photos.
Thanks for linking up with #wkendtravelinspiration! Hope to see you next week as well!
Wow – those photos are stunning. Vermont is so vibrant and beautiful.
What a beautiful place to live. I haven’t had the pleasure of visiting anywhere in Vermont as yet. My home town is very different to yours – I live near the beach in Australia! 🙂
One of the best part about connecting with other bloggers is becoming an armchair traveler. I’d love to go to Australia.
WOW!!! Vermont is so beautiful. I have always wanted to visit and this makes me think I need to just do it already. I totally agree about how difficult it is to write about my hometown. Its an amazing place but its like I try to keep it a secret. I am working on it 🙂
Wow, you’re photos of Vermont are stunning!! Especially the first one! Vermont has been on my list of places to visit in the fall, I’m gonna make it happen in 2016. Thanks for all the cool spots to visit. 🙂
We were in Stowe, Lower Waterford, Brattleboro and other places in Vermont, but not Bennington. Looks like we missed yet another stunning place.
You picked some beautiful towns to explore, Paul. I’ve never been to Lower Waterford, but I love Stowe and Brattleboro.
I’ve only been to Vermont twice in the two years I lived in New England. I wish I had gotten to see more.
I am a lover (and active searcher) of small towns. It is incredible how much beauty is in and around the town. I see why you are so proud of writing about it. Yes, sometimes it is not easy to write about a place that occupies a special place in your heart. it is like you cannot organize the thoughts you want to convey in a proper way.
Me too, Ruth. I love making those little discoveries on my own and thinking, “wow, nobody knows about this place but me.”
I can see why you fell in love with Vermont! Wonderful State Parks and historic monuments for you to explore. Beautiful photos, I love all of them!
Thanks, Brooke!
What a great post! I come up every year around Bennington Battle Day for a family reunion and have been to every place on your list with the exception of The Old First Church. I’ll have to try to check it out this year. Also, your photography is beautiful! I’ve followed you on Instagram so I can go and enjoy more of it. Would you mind if I shared this post on my Facebook page?
Megan,
It’s cool to hear from someone who actually knows Bennington! Funny thing is we’ve never been to Battle Day. We’re always out of town or trying to avoid the crowds. I would definitely appreciate a share! Thanks so much.
Such a pictureque place. Some of my mother’s ancestors lived in that part of the country before they moved west several generations ago. I’ve always wanted to take a trip there to see it, but haven’t quite made it yet.
I’ve always wanted to go to Vermont and these pictures seal the deal! I’d love to do a road trip from Boston up to Vermont. Hopefully someday soon!
Karin, we’re just under 4 hours from Boston. You can do a great loop in Southern Vermont. You don’t have to wait for leaf-peeping season. Summer would be just right…
http://backroadramblers.com/a-leaf-peeping-road-trip-in-vermont/
Wow! The colors are exquisite!! I’ve never been back east but my husband keeps telling me we need to go! Now I understand why! Love this!!
Thanks, Julie!
Your hometown is gorgeous! It reminds me of my own, especially when it comes to the nature.
I’m interested in doing a guest post! 😀 I’m originally from a small town in northern Ontario, Canada. I did a Photo Friday post about winter in my hometown last week – http://www.trekkingwithbecky.com/winter-hometown-kapuskasing/ Would you be interested in a small town from northern Ontario featured in a guest post? 😀
Becky,
I would love to have you do a guest post. I read your last post about winter in your hometown. And I thought Vermont got cold! Would you mind filling out the form on the guest post page so I can keep track? Pick whatever date you want. I’ll cross off the dates that are taken.
What a great idea! Let me think a little bit about it and I very well might be interested in doing a guest post 😉
Your hometown looks like a wonderful place to visit! I’m going eventually get that direction. May take us a couple of years, but we will 😉
Thanks for sharing with us at Photo Friday!
Jen, if you are ever up this way, be sure to contact me. I’ll show you around and maybe we could do a Photo Friday field trip.