Vermont Fall Vacation – 2020

We had such a wonderful time on our Vermont Fall Vacation. If you missed the first part of our fall vacation recap, you can check it out here.

Our Vermont Fall Vacation

Our Vermont vacation destination was the fabulous Woodstock Inn and Resort in Woodstock, Vermont.

The Woodstock Inn in Woodstock, VT

We enjoy staying at The Woodstock Inn for several reasons.

  • We love the entryway with its large fireplace, the library, and other comfortable areas for relaxing out of your room.
  • The rooms are not only beautiful but also comfortable. There is a dog-friendly wing, so Sherman can come on vacation with us and enjoy all areas of the inn except the two restaurants, so staying there works very well for us.
  • There are two mountains within walking distance of the inn, both with many trails for hiking.
  • We love walking around the village of Woodstock to shop and to admire the old houses.
  • There are tons of fun things to do in the Woodstock area, all a short drive away.

Last year we also vacationed in October at The Woodstock Inn. To see pictures of the interior of the inn and our room visit that post. You’ll also see some fabulous fall foliage in the post, way more brilliant than what we experienced this year.

After enjoying Maryland, Pennsylvania, and New York, it was on to Woodstock, Vermont for the week.

Dog riding in a car on a dog bed

Fall Vacation in Woodstock, Vermont

The number one thing I love about The Woodstock Inn is sitting in front of this fire in the morning. Each day of our vacation, I headed here the second my feet hit the floor.

Fireplace at Woodstock Inn in Woodstock, Vermont

Mr. SP took Sherman for a short walk and then joined me. I honestly could sit in this spot all day long and be perfectly satisfied.

Woman and dog enjoying the fire at Woodstock Inn in Woodstock, VT

Having a dog encourages others to talk to you. We talked to many inn guests that we wouldn’t have otherwise if it weren’t for Sherman. It was fun to run into the same guests in town or on the trails.

Sherman enjoyed our morning coffee time as much as we did.

Sherman Skulina enjoying the foyer at The Woodstock Inn, Vermont

The inn is beautifully decorated with touches of fall added in different spots.

Fall decor in The Woodstock Inn

The inn has incredible gardens where both food for the restaurants and pumpkins and gourds used for decor are grown.

Fall decor in The Woodstock Inn

Daily Hikes

After coffee, each day we took Sherman on a hike. Since this was our fourth fall trip to The Woodstock Inn, Sherman knows the trails and we let him lead us on that day’s hike.

Dog posing by a rock wall in the woods

The Pogue on Mount Tom

A favorite spot is The Pogue on Mount Tom. Mount Tom has carriage trails built by the Rockefellers, one trail leads to The Pogue.

This spot is beautiful in the fall.

Hiking at The Pogue on Mt. Tom in Woodstock,VT

The leaves started changing earlier than normal in Vermont this year. We were there the week before Columbus Day which is typically the peak of color. While gorgeous, the foliage wasn’t as vivid as we enjoyed last year.

There are no complaints from me because the foliage was still pretty spectacular.

Fall foliage at The Pogue on Mt. Tom in Woodstock,VT

The trail goes around The Pogue so the view can be enjoyed from all sides. Sherman always takes advantage of the situation and goes for a swim and gets a drink of water.

Fall foliage at The Pogue on Mt. Tom in Woodstock,VT

The Star on Mount Tom

Another Mount Tom hike that we enjoy is hiking to the star.

Star at the top of Mt Tom in Woodstock, VT

This is a popular spot because of the view of the town of Woodstock and neighboring areas.

Town of Woodstock, Vermont from the top of Mt. Tom in fall

Visiting Woodstock feels like being in a Hallmark movie. It’s so charming!

The mountain behind the town is Mount Peg, another wonderful place to hike.

View of the town of Woodstock, Vermont from the top of Mt. Tom in fall

Some people like a beach or tropical island vacation, for me paradise is the mountains.

Fall foliage in Woodstock, VT from the summit of Mt. Tom

The top of the mountain is a great spot to rest and enjoy the view.

Man and dog enjoying fall foliage at the top of Mt. Tom in Woodstock, Vermont

We had great weather on our trip, no rainy days, and mostly clear skies, perfect for enjoying the views and the foliage.

Enjoying fall foliage at the top of Mt. Tom in Woodstock, Vermont

Because we hike with Sherman, we end up talking to other hikers with dogs.

One hiker who has a second home in the area was super nice and Sherman took a liking to his dog, Roxie. He found one of my Instagram posts and we became Instagram friends which led him to inviting us to hang out around his firepit with a mountain view on our next Vermont trip.

Fall foliage in Woodstock, VT seen from the summit of Mt. Tom

More Scenes from Mount Tom

We hiked on Mount Tom three mornings and on Mount Peg two mornings.

This shot was taken walking to The Billings Farm where one of the trail accesses is located.

Fall foliage in Woodstock, VT

This is one of the carriage trails. The carriage trails are wide and there are hiking trails leading into the forest off them.

Woman and dog on a carriage trail on Mount Tom, Vermont

Fall in Virginia is pretty, but we don’t have brilliant reds like this in my area of the state.

Fall foliage in Woodstock, VT

This tree is mostly likely bare by now.

Red maple foliage in Woodstock, VT

When Sherman takes a hiking break, I can’t resist taking a picture of him.

Dog sitting in the woods

Hiking the trails is activity that the three of us enjoy so much.

Hiking on Mount Tom in Woodstock, VT

Sherman is a very affectionate dog and a rest session almost always includes some kisses.

Hiking Mount Tom in Woodstock, VT

Here he is resting after a long climb.

Dog laying down in fallen leaves

This Mount Tom trail gives a view from the other side of the mountain.

Couple with fall foliage in the background

Hiking Mount Peg

The other mountain that we like to hike is Mount Peg. A few trails lead to the summit which leads to many cross country ski trails to hike.

Fall summit view Mt. Peg

There are benches at the top, picnic tables, and even a fire ring for an evening bon fire. The trail in the background leads to the cross country ski trails.

Woman petting dog at the summit of Mt. Peg in Woodstock, Vermont

Sherman and I love this view. We intended to hike here to see the sunset but never did.

njoying the view from the summit of Mt. Peg in Woodstock, Vermont

On one of our Mount Peg hikes, a mother and her two kids were enjoying the view from this spot.

Sherman is almost always a kid magnet.

Dog being petted at the summit of Mt. Peg in Woodstock, VT

This sweet little girl who was visiting Vermont from Arkansas really liked Sherman.

Dog being hugged by a young girl we met while hiking Mt. Peg in Woodstock, VT

She was the sweetest little girl and the loved on Sherman for a good while.

Little girl hugging a dog

The foliage along the cross country ski trails was very pretty. I’ve only cross country skied once and there’s no way I could ski these trails. When Mr. SP was in grad school at University of Wisconsin, he skied to class.

Fall foliage on Mount Peg, Woodstock, VT

Afternoon Adventures

In the afternoons, we visited some of our favorite spots.

Vermont Country Store

We can’t visit Vermont without a visit to The Vermont Country Store. On our past Vermont fall vacations, the store has been filled with tourists and also with people on tour bus trips.

This year there were no crowds and also no samples of cheese and other goodies.

Couple and dog at The Vermont Country Store

We both love browsing the store and we especially love that it is dog friendly.

Shopping at The Vermont Country Store with a dog

On a previous afternoon, we drove to the Darn Tough (the best socks ever) factory in Northfield thinking that there would be a factory store. There was no store but we did enjoy the drive and enjoyed lunch in Northfield, home of Norwich University.

While at the Vermont Country Store, we treated ourselves to a few new pairs of Darn Tough socks. If you have never tried this brand, do it! They are so comfortable and they wear like iron.

Quechee Gorge

We always enjoy a hike down to the Ottaquechee River in Quechee Gorge.

Quechee Gorge in Quechee, Vermont

This is a popular spot and even with drastically reduced tourist crowds this year, it still was full of people and dogs.

Hiking Quechee Gorge in Quechee, Vermont

Sherman enjoys this hike for the swimming opportunities.

Hiking Quechee Gorge in Quechee, Vermont

Sugarbush Farm

Another favorite spot to visit on a Vermont fall vacation is Sugarbush Farm. The view here is pretty and they make cheese and maple syrup, with samples available to try.

You can walk around the farm and also enjoy a self-tour to see where they make maple syrup in the spring and you can also walk into the woods to see the tapped maple trees.

Sugarbush Farm in Woodstock, VT

We love sampling cheese here and we were delighted that sampling was allowed this year.

Fall foliage at Sugarbush Farm in Woodstock, VT

After buying cheese and enjoying the view from the farm, we headed off for another adventure.

Fall foliage at Sugarbush Farm in Woodstock, VT

Foliage Seen from Okemo Mountain

We love driving to the top of Okemo Mountain in the fall to admire the foliage. The open space is a ski slope in the winter.

Fall foliage along the ski slopes of Okemo Mountain, VT

In winter it is freezing cold at the top of this mountain. The long ride up the ski lift is a cold one.

Fall foliage at the top of Okemo Mountain

In winter when you get off the ski lift for the first time and see this view when snow covered, you have to stop to admire it before taking your first run down the mountain.

Selfie from the top of Okemo Mountain, Vermont

We haven’t skied Okemo in a few years because of Sherman.

Ski lift, woman, dog on the top of Okemo Mountain, Vermont

Our big baby has to go on vacation with us because he got uninvited back to the kennel where he used to stay and we don’t think he could tolerate a dog sitter.

Fall foliage seen from the top of Okemo Mountain, VT

Sherman gets anxious when we leave him in a place besides home, so we haven’t tried renting a dog-friendly condo at Okemo.

Another popular ski resort near Woodstock is Killington. My brother skied Killington once and loved it.

My friend, Shelley, of Calypso in the Country, has a place there and she and her family love to ski Killington’s many trails.

Since we had never seen Killington, we drove there one afternoon. The trails are now covered in snow and their projected opening date for skiing is November 14.

Fall foliage in Vermont

Enjoying the Town of Woodstock

We so much enjoy walking around the town of Woodstock. Sherman saw some cows at The Billings Farm that he was very interested in chasing.

Man and dog at Billings Farm in Woodstock, Vermont

We didn’t tour the farm this year but did enjoy walking around the grounds.

Couple and dog at Billings Farm in Woodstock, Vermont

The town of Woodstock is so charming and residents and businesses go all out for fall decorating. See more of the town’s fall decor in this post.

Pumpkins on the top of fence posts in Woodstock, VT

Most of the shops are dog friendly which makes shopping with Sherman much easier.

Dog friendly bookstore in Woodstock, VT

Mr. SP had to work a few hours each day and we both enjoyed working from the inn’s library.

Enjoying the library in the Woodstock Inn in Woodstock, VT

This trip was another fabulous Vermont fall vacation and we couldn’t have enjoyed it more.

Other Vermont Vacations

These are posts that I’ve written about other Vermont trips. We’ve been vacationing there since our honeymoon in July 1994.

Fall Mountain scene from Okemo Mountain, Vermont

If you’ve ever thought about taking a Vermont fall vacation, I encourage you to do so. The foliage is fabulous and there are so many fun things to do in different areas of the state.


  1. You guys have me wanting to book a trip NOW!! There are three particular pictures that just warmed my heart thoroughly; The photo of you and Sherman from behind as you two are looking out over Mt. Tom (I’m pretty sure that’s where you are!), the photo of you, Mr. SP and Sherman towards the end and the picture of the little girl from Arkansas hugging Sherman and him leaning into her!!! It reminded me of our sweet Molly who we loved beyond works.
    You look great Paula and I and do hold you in prayer for total healing.

  2. I soaked in all the details of your trip, Paula. Mr, P & I would love this trip. Those socks – pinned, especially for Mr. P. He has to have something sized longer than a 14 in men’s (XL), and I was happy to see they can do that! Love that Sherman goes with you and that the entire trip is dog-friendly. Also loved your jacket. I can see it’s LLBean, but is it down or packable primaloft? Looks like the perfect transitional jacket to be able to move in.

  3. I love Woodstock too! Especially Billings Farm! Your dog is so cute. Thanks for posting about your beautiful trip.

  4. Hi Paula!
    My husband skied Killington once before we were married. I think he had a good time. What a full vacation you had! That gorge was beautiful!!


  5. Oh my goodness, Paula! I’ve always wanted to visit New England in the autumn, but I’ve never done so. . . now my tongue is hanging out! Well, I shouldn’t say I’ve never been to NE in the autumn–I did go to Newport, Rhode Island for my son’s graduation from Officer Candidate School, but that was in November, so it wasn’t a particularly pretty time to go. Anyway, THANK YOU for taking us along on this trip. What wonderful memories y’all have made! And thanks for letting us see all your fun with Sherman. Now that Snickers and Cocoa have crossed over the Rainbow Bridge, we’re thinking about getting another dog. . . but this time, we want to try our dog to travel with us.

    Thanks so much for joining the Grace at Home party. I’m featuring you this week!

  6. Paula, I know this post was from a year ago, but it is sooo timely and beautiful! I had to include it in this past week’s Share Your Style #323 for you!!! <3 I love that you can walk so many different trails and many of the shops are dog friendly. That makes it so much easier! Yoda can't board anymore either… He panics and cries and then needs calming meds. It took 1 1/2 hrs. to calm him after our trip to California this summer (June 2021) for Pete's funeral/help Gini (my MIL) prep her outside of the house and sheds/garage for sale. She's moving here to Texas!

    Anyway, I hope you are doing well. I saw a recent photograph of you sans your lovely hair… Cancer sucks… I do hope this is a good round of treatments for you! And I shared a bunch of your photographs on many of my Pinterest pages. Makes me want to go on a long trip… <3

    Love and hugs,
    Barb 🙂

    1. Thank you so much for pinning from my post! I hated to miss fall in Vermont but it was wonderful to go out west. Poor Yoda! It distresses me when Sherman is uncomfortable or in pain.

  7. Paula, I’d love to stay at the Woodstock Inn sometime. I love that it’s dog friendly! Vermont is so beautiful in the Fall. Thanks for sharing at Celebrate Your Story! Link Party. You’ve been featured this week 🙂

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