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7 Beautiful Places to Visit in Bennington, Vermont

Fall Foliage Photography in Southwestern Vermont

The View of Mt. Anthony from the bypass in Bennington

Does anyone else find it harder to write about a place you know and love intimately than it is to write about new and intriguing places you find while traveling? I’m having that issue today, but I really want to share my hometown with you, especially the special outdoor places that make Bennington so special. 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.

The photos in this post are taken from my Instagram account .  My gallery is very “Vermonty”, with a few other lovely places sprinkled throughout for good measure.

Fall Foliage Photography in Southwestern Vermont

Woodford State Park, Woodford, Vermont

My Hometown: Bennington, Vermont

Until now, I’ve never really had a hometown. I’ve lived in dozens of places all over the country, never really settling in until I came here. I discovered this special place quite by accident thanks to house shopping on the internet. When we were looking to buy our first house back in 2006, we naturally spent hours each day browsing real estate websites. We were originally looking in the Hudson Valley of New York, and every weekend we would slog around with realtors looking at dumpy houses that we couldn’t afford.

We slowly started widening our browsing circle and found ourselves exploring Bennington, Vermont. We fell in love with a cute little bungalow on our second trip to town, and we never looked back. Okay, we did look back a bunch, but mostly we looked forward.

Bennington, Vermont

Headwaters Park, Bennington, Vermont

Bennington took me by surprise, and we chose to hunker down and raise a family here. Amazingly, I’ve lived here longer than any place I’ve ever been – 10 years this spring. So even though we’re set on exploring the world near and far, I have to tell you a bit about my home town.

Bennington, Vermont is Gorgeous in Just About Every Season

Bennington, Vermont

Meyers Road, North Bennington/Shaftsbury Vermont

I say just about, because I’m not terribly fond of mud season. I’ve lost whole boots to muddy quagmires, and I’ve known others that have lost cars! Luckily, mud season is short, lasting the month of March, and as long as we keep climate change at bay, I think I can handle it. Lucky for us, mud season goes hand-in-hand with maple sugaring season, so I guess that’s reason enough to cut it some slack! 

Bennington, Vermont

Overlea Road, North Bennington, Vermont

7 Beautiful Places to Visit in and around Bennington, Vermont

The Old First Church

Bennington, Vermont

The Old First Church, Bennington, Vermont

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, and Old Bennington in general is such a lovely place to explore, even if you’re not visiting during leaf-peeping season.  

 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. 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 foliage season.

Be sure to visit the grave of one of our most famous residents, Robert Frost, which is located in the beautiful old graveyard between the Old First Church and the Bennington Museum

Bennington, Vermont

Robert Frost’s grave behind the Old First Church, Bennington, Vermont

The Bennington Battle Monument

While you’re in Old Bennington, you won’t want to miss a tour of the Bennington Monument. 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. Visitors can ride to the top in an elevator from mid-April unitl 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.

Bennington, Vermont

The Bennington Monument from the Old First Church

The Robert Frost House

He’s buried in Bennington, but he lived in a little stone house in Shaftsbury, the next town over. You can walk through the house in five minutes or so, but there’s also a beautiful nature trail that starts behind the barn and heads out to Lake Paran in North Bennington. The trail is 2 miles, one way.

Lake Shaftsbury State Park

While you’re in Shaftsbury, please take a walk around the lake at Lake Shaftsbury State Park. You can bring your dog in the off season, and in the summer you can go for a swim.

Lake Shaftsbury in Autumn

Woodford State Park

Another gem, this one is 10 miles outside of Bennington, in the Green Mountains. If you’re camping, Woodford State Park is where you want to do it. The lake is cold, even in summer, but it’s such a paradise! In my opinion, this is one of the most beautiful places in Vermont.

Woodford State Park

The Appalachian Trail

The famous long-distance trail runs across route 9 between Bennington and Woodford. There’s a parking area right off the road. The trail runs north and south, but we prefer hiking south to Harmon Hill, for the beautiful views of the town.

Birches - Appalachian Trail, Bennington

Park McCullough House

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-the-Woods hiking trail all in one visit. This is one of my favorite places to walk and take pictures, and we always bring visitors here.

Park McCullough House

photo credit: Angus McCullough

Park McCullough House

photo credit: Angus McCullough

As usual, I focused almost entirely on outdoor excursions, but there are also cool museums, lots of shopping, and good restaurants. If you really do come to Vermont for a visit, feel free to contact me. I’d love to show you around!

Resources for Exploring Bennington, Vermont

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.

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 stayTrivago has great low prices for hotels in Bennington. If you want to camp, we highly recommend Woodford State Park.

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If you're visiting the Green Mountains, you have to check out Bennington, Vermont. Such a beautiful town in all seasons!



  1. 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!!

  2. stacey t

    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!

  3. Allen

    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.

  4. Erica Haye

    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.

  5. Kathy

    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?

  6. Jane Griswold Radocchia

    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!

  7. 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.

  8. i haven’t been to VT in a while. Great reminders of why I like it! and thanks for joining #wkendtravelinspiration
    eileen g recently posted…7 Best Tips For Fun Ski Trips With KidsMy Profile

  9. Picture postcard gorgeous! I had no idea Vermont was so beautiful. You made the right choice!

  10. I love these pictures! Vermont is such a beautiful place!

  11. 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.
    bettyl-NZ recently posted…Tupare GardensMy Profile

    • 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!

  12. 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.

  13. 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

  14. 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 |

  15. 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!

  16. I want to visit Vermont so bad! Gorgeous photos.

  17. Vermont certainly is a gorgeous state! Love, love, love your photos.
    Corinne recently posted…Searching for BeautifulMy Profile

  18. Wow – those photos are stunning. Vermont is so vibrant and beautiful.
    Rhonda Albom recently posted…Enjoy These Far North Restaurants in New Zealand – WTIMy Profile

  19. 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 🙂
    Mama Munchkin (@globalmunchkins) recently posted…Steamboat Springs BucketlistMy Profile

  20. 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.

  21. Jia

    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. 🙂

  22. We were in Stowe, Lower Waterford, Brattleboro and other places in Vermont, but not Bennington. Looks like we missed yet another stunning place.
    Paula McInerney recently posted…Millennials have Discovered B & B’s and are Loving ThemMy Profile

  23. I’ve only been to Vermont twice in the two years I lived in New England. I wish I had gotten to see more.

  24. 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.
    Ruth recently posted…Valencia: Mercat CentralMy Profile

  25. 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!

  26. 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.

  27. 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.

  28. 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!

  29. 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!!

  30. 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 – 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.

  31. Jen

    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 recently posted…Photo Friday – Brown PelicansMy Profile

    • 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.

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