Our Fall Vacation in Woodstock, Vermont
We just got back from a fall vacation in Woodstock, Vermont and today I’m sharing details from our trip. Today’s post will be about the things we did in Vermont and the beautiful fall foliage that we saw.
Tomorrow I’ll be back to share fall porches and other decorations that I spotted that are too pretty to keep to myself. In Vermont people go all out decorating for fall and I really enjoyed the decor that I saw. (Update – Read all about the fall porches and decorations that I admired here.)
Our Fall Vacation in Woodstock, Vermont
We got really lucky this year and the foliage was just about at its peak in Woodstock, Vermont where we stayed. This is a picture heavy post and one I’m writing not only to share with you, but also for myself because I love to look back at travel posts that I’ve written to relive a great trip like this one.
Where We Stayed in Vermont
We have traveled to Vermont many times and our favorite town to enjoy is Woodstock, Vermont. We stay at the beautiful Woodstock Inn, our favorite hotel anywhere, who gets bonus points for being dog friendly.
Sherman travels with us and the Woodstock Inn has a few dog friendly rooms for their furry guests. Dogs are allowed everywhere in the inn except for the two restaurants.
We arrived on a Sunday evening and there was a line of people waiting to check in to the inn. I was in line with Sherman and would you believe that a man in line with me recognized Sherman from a previous visit? The staff at Woodstock Inn really liked Sherman and greeted him every time they saw him.
Sherman made himself at home immediately in the room. I always bring a sheet to put over the bed to protect the inn’s linens but Sherman hopped onto the bed before we could unpack it. Doesn’t he look content?
We spent every morning and evening in front of the fire in the lobby of the hotel. 
The Woodstock Inn has places to relax all around the lobby area. Some people say that they want to retire to a cruise ship. I think that I could retire to the Woodstock Inn and be quite content.
The great thing about traveling with a friendly dog is that many people see your dog and want to pet him which leads to conversation. We enjoyed meeting people both morning and evening and that wouldn’t have happened had we not been traveling with Sherman.
You can see that Sherman is quite comfortable at the Woodstock Inn.
Sherman got loved on by so many people. 
Morning or evening, Sherman enjoyed the lobby of the Woodstock Inn along with us.
This is another seating area in the lobby of the Woodstock Inn.
We spent several evenings in the library enjoying a cocktail before dinner. Speaking of dinner, Sherman complicates that a bit, so we ate most of our evening meals in our room. We got takeout from Richardson Tavern in the inn twice, food from Woodstock Farmer’s Market twice, and left Sherman in the car while we enjoyed two other meals, one at DJ’s in Ludlow and the other at Worthy Kitchen in Woodstock.
Our Typical Vacation Day in Woodstock
Since we have Sherman with us, a good bit of our vacation time revolves around making him happy. Making Sherman happy makes us happy, so it’s a win-win situation.
After morning coffee we hiked with Sherman either on Mount Tom or Mount Peg both of which are located within walking distance of the Woodstock Inn. Both mountains are filled with trails that are beautiful.
Sherman leads the way for his morning walk and most days he chose to hike Mount Tom which we access by walking through the Woodstock Middle Bridge.
This is the view from the bridge on a foggy morning.
Here’s the same view on a clear morning.
The street leading to the trails on the mountain was full of color and also full of beautiful homes.
Hiking on Mount Tom
We got lucky on this vacation and only had rain on the first day. Even in the rain the leaves were pretty. This is The Pogue, a pond on Mount Tom.
The next day the sun was out, the sky was blue, and the foliage was brilliant on the mountain surrounding The Pogue.
Sherman enjoys this part of the hike because he gets to swim and get a drink of water.
It’s hard to capture the beauty of the leaves with a camera but in this shot you can see how brilliant the colors were.
When you’re in love with your fur baby, you have to stop to take numerous pictures of him while hiking.
Sherman is a very affectionate dog. Look at him looking at him Mama!
Summit of Mount Tom
The reward for hiking Mount Tom is this beautiful view of the village of Woodstock.
Two out of the three times that we hiked to the summit, we encountered a group of hikers from Backroads, a touring company that was also staying at the Woodstock Inn. It was great to have company at the top to ask for a family picture to be taken.
We’ve enjoyed the views from this summit in every season except spring and they are all beautiful but fall is my favorite.
Fall Foliage on Mount Tom
Many of the trails on Mount Tom are carriage trails built by the Rockefellers. 
Every step on these trails had something beautiful to enjoy.
More on our Typical Day in Vermont
After our morning hike, it was lunchtime, so each day we headed out in the car for lunch and then a destination. Two days we ate lunch at South Woodstock General Store in Kedron Valley. The sandwiches here were great and both days we ate them while sitting on the store’s front porch.
This is an old school near the general store. The store is beside the Kedron Valley Inn, a beautiful inn seen on a Budweiser commercial years ago. We once stayed there on a bike trip and really enjoyed it. Be sure to come back tomorrow to see some outdoor fall displays that I enjoyed seeing in this area.
Okemo Mountain Summit
One of our afternoon trips was to the summit of Okemo Mountain. We’ve skied here many years and enjoy seeing the slopes and the fall foliage when they aren’t covered with snow.
We haven’t taken a ski trip since Sherman was kicked out of the posh kennel where we used to board him when we vacationed. He is very attached to us and was in distress the last time we left him at the kennel and we had to cut that trip short and come home to rescue him. Since then Sherman goes where we go. If Sherman can’t come, we don’t go.
Beautiful color could be seen for miles and miles.
This shot was taken on the way down the mountain. The cleared area is a ski slope.
Jenne Farm
Another day trip was to see Jenne Farm, the most photographed farm in Vermont.
The views from the hill above the farm were beautiful.
The Vermont Country Store
On every Vermont vacation we visit The Vermont Country Store. This is a very popular spot for tourists and also a stop for tour buses. It was very crowded, so we didn’t stay long. We stocked up on our favorite Darn Tough socks and I bought one thing that you’ll see when I decorate for Christmas.
We also walked Sherman around the town of Weston which led to talking to other tourists which is always fun.
Jacket | Boots | Jeans and Sweater
Foliage Seen on our Drives
On our afternoon drives we saw beautiful foliage. This shot was taken on our way to Ludlow and the Indian tent in the backyard always fascinates me. It’s been in the yard for years and I always wonder what the story is behind it.
We stopped at Hawk’s Inn and Mountain Resort to take this picture by one of their ponds. We’ve been in Vermont three falls in a row and each fall this place is empty. Their website is under construction so perhaps there is a new owner who is going to get it going again.
Sherman got in this pond for a swim moments after I took this picture.
Boyden Valley Winery
Last year I bought a bottle of delicious Vermont Maple Reserve wine from Boyden Valley Winery at F. H. Gillingham and Sons general store in Woodstock. I liked it so much that I saved the bottle so I would remember the winery to visit on this trip.
Boyden Valley Winery is in Cambridge, Vermont, almost two hours away from the Woodstock Inn. It was a long trip to get there, but we made the most of it by stopping in Montpelier for lunch and walk around town, and then enjoying fabulous fall foliage as we drove.
We enjoyed tasting wine and walking around the farm. I wouldn’t hesitate to return to this winery.
Hiking on Mount Peg
Sherman enjoyed a long walk each morning either on Mount Tom or Mount Peg. Mount Peg is located behind the Woodstock Inn and is covered with both hiking and cross country skiing trails. This shot was taken on a morning Mount Peg hike.
Sherman hurt his leg at the end of our trip so we tried to not let him walk very far. On our last evening in Woodstock, he insisted on hiking to the top of Mount Tom. His leg loosened up as he walked and he had no problem hiking the one mile to the summit of Mount Tom. We were so happy that led us to the top because the evening views were gorgeous.
Sherman seemed to enjoy the views as much as we did.
You can see that we’re walking in our street clothes rather than athletic wear. I was worried about walking up a mountain in the new boots that I was wearing but they ended up being 100% comfortable for a hike. The boots are Blundstones and I bought them because me dear friend and former running partner (sigh, I miss running so much) has worn them for years and when she vacations, these are the only shoes that the brings.
Suzanne and I along with her twin Theresa are going on a trip next month and these boots will definitely be on my feet. I may even only take them, they are that comfortable.
Seeing the evening light on the summit of Mount Tom was the perfect way to end our Vermont trip.
We both love traveling to Woodstock and I’m already looking forward to when I may get the chance to return there. We’ve never traveled to Vermont in the spring for sugaring season, so perhaps we’ll travel there this spring.
Be sure to come back tomorrow to see beautiful fall outdoor displays that I photographed on our trip. (Update: See the beautiful fall outdoor displays here.)
Paula, your pictures are stunning! You picked a great week to go with the foliage at its peak. Those views from the top of the mountain are gorgeous. One of these days, I really need to take some hikes…maybe when I am up there in summer or fall. And the Woodstock Inn is such a fabulous hotel. Not only is it beautiful but I love that it’s dog friendly. Sherman is definitely living the good life! Loved your post!
Shelley
Thank you, Shelley! We really enjoy hiking from Woodstock and also staying at the Woodstock Inn, but who wouldn’t enjoy that?? Sherman had a great vacation and he’s looking forward to going back. Have you ever been for sugaring season? I thought that might be fun to see.
Paula
Paula such a fantastic display of your week in Vermont. Judy and I know you both enjoyed your trip and so did Sherman.t
Thank you Tom and Judy! We had a fabulous trip and so did Sherman.
Paula
So beautiful! I love how you bring Sherman with you. He is adorable! The pics are gorgeous! I need to plan a trip to Vermont in the Fall. We have been in Summer and Winter but not Fall. Need to put that on the bucket list. Thanks for sharing your trip. 🙂
When I was still teaching, I was the same way,. I’d been to Vermont in July and December, but never in fall. When I retired due to my cancer, my husband made a fall trip happen for me and I’ve been blessed to go 3 falls in a row. I hope you plan a trip for next year.
Paula
Your pictures are incredible! You picked just the right time to visit Vermont. I love the photographs of the Inn where you stayed. It looks like an elegant place.
It is a wonderful place to stay. In fact, I think I could live there. 🙂
Paula
Hi Paula,
It looks as though you had a relaxing time. The photos are absolutely gorgeous! I am so happy to hear you got good news! Praying for you 🙂
Thank you so much for your prayers. I definitely need them with this roller coaster I am on with my cancer. We had a great time and I already miss being there.
Paula
WOW! Your photos are stunning! I’d love to visit Vermont someday.
Thank you so much! It is a wonderful place to take a vacation.
Paula
Fantastic health news, Paula and a lovely getaway. Vermont is one of the places I would love to visit. I’ve been to Maine,, in the summer, along the coast; totally different kind of beauty. The colors of Vermont, in autumn, are breathtaking. We planted two red Maple trees hoping to get the Vermont look but it just ain’t happening in the Savannah, Georgia area. Thy re pretty but nothing like your beautiful photos. Looking forward to seeing more.
Thank you so much, Shirley! You are right about the red maples. I have a red maple in my backyard and it’s pretty in fall, but definitely not as pretty as a sugar maple. I published a follow up post to this one sharing more of Vermont and I hope you enjoy it.
Paula
Paula this is such a beautiful post. Don’t you luv Vermont😉 I used to hike Mt Tom in college and have enjoyed all the spots you mention. Such a happy place❤️❤️❤️Pinning!
I love that you hiked Mt. Tom in college. Your state is wonderful and we love visiting there. The next time we will have to do more exploring in your area.
Paula
Wow! Beautiful inn, beautiful location and beautiful Sherman! Thrill with you that you’re stable. Linda
Thank you so much, Linda! Stable is a wonderful word when you’re in my situation.
We had so much fun in Vermont and Sherman did as well.
Good to hear from you!
Paula
So many beautiful photos! I completely agree that the camera just does not do the colors and views justice as I have been trying all month long to get a “good” shot of all the beautiful fall colors around us.
Isn’t it funny how you take a picture and look at it and think, “Why isn’t it showing how great these leaves look?” The leaves here in VA are just starting to turn and I’m hoping that soon we’ll have some pretty color here.
Paula
What beautiful photos! I love New England and Vermont is especially beautiful.
Thank you, Donna! We had such a great trip to Vermont.
Paula
Thank you so much for sharing your vacation with us. Sherman lives better than a lot of people! I have not been to the Woodstock area; but we have been to the Burlington/Barre/Montpelier, and Shelburne areas. Love the Shelburne Museum to see how earlier Americans lived! When I think of fall colors, I think of Vt, although I grew up in NH and live in Maine. My house is surrounded by sugar maples–pretty much naked now due to wind and rain.
I haven’t been to the Shelburne Museum in years. I really liked it and the next time we go to VT, I’m going to make a visit there.
I think we got very lucky with the leaves this year. The week after we came home, Vermont had a lot of rain and I heard that the leaves came down.
Sugar Maples are so pretty. There are some here in Virginia but Vermont’s are definitely prettier!
Paula
Paula, I saved this post so I could read it in lazy time. I loved your Vermont trip and how you keep Sherman as part of your family while traveling. Nothing worse than a furbaby in distress. Those effects last beyond its person’s absence! Great color in VT. We’re just getting near peak here in WV. Bridge Day was this weekend at the New River Gorge in Fayetteville – the 40th anniversary of base jumpers free falling 876′ off the bridge. I rather like the type of trip you had – the leisurely hikes, enjoying the views, even meals in the room wouldn’t bother me one bit! Glad you had a good trip.
I haven’t seen the New River Gorge bridge in years. When I was at Virginia Tech, I had a friend who loved to drive. We drove there a few times and it never failed to impress me. My other time seeing it was from the river and my first and last white water rafting trip. Anyone who jumps off of that bridge is nuts!!
Paula
You sure got some amazing photos, Paula… I would LOVE to visit Vermont someday. Maybe a mother/daughter trip? Thanks for sharing. Pinned!
A mother/daughter Vermont trip would be so much fun. I really would like to take my mom there. She’s been twice but I’d like to show her the things that Dave and I like to do there.
Paula
Looks like an amazing time was had by all! Such a beautiful place. New England is on my Bucket List. It is always nice when you can travel with your fur babies.
It’s great to be able to take Sherman with us. We had a wonderful vacation!
Paula
Paula, your photos of the Vermont foliage are gorgeous! It’s nice to know the Woodstock Inn is dog friendly. I’d love to go there sometime with our 2 dogs. I especially love the photo of Sherman swimming…our Golden Retriever is a swimmer, too. I’ve always wanted to check out the Vermont Country Store. Thanks for sharing! I’m so glad you’re doing well and had such a wonderful time 🙂
Thank you, Rebecca! It’s nice to find a dog friendly place to stay. We usually end up at LaQuinta because they’ll take dogs of any size. Woodstock Inn is definitely a step up from La Quinta. The Vermont Country Store is a fun place to visit. I was good this year and didn’t buy too much there.
Paula
Such a great post! Looks like you all had a wonderful trip! Sherman looks like he enjoyed his time in New England. Vermont is gorgeous…especially at this time of year!
We had such a good time and Sherman enjoyed the trip along with us. We got really lucky and caught the leaves at their peak.
Paula
Paula your pictures are absolutely gorgeous. I have always wanted to visit Vermont , maybe one day.
Thank you, Sonya! We love traveling to Vermont, it’s so pretty. I hope that one day you’ll take a vacation there to see its beauty.
Paula
Such beautiful pictures– and I love seeing the ones both in the fog and without. This post was the most clicked last week at Best of the Weekend! Congratulations!
Liberty @ B4andAfters.com
Vermont in fall was wonderful! I’m so excited to be the most clicked for last week. I used to love to see which post was most clicked when I was writing my weekly BOTW post.
Paula
Beautiful! My family and I traveled to Vermont for the first time this past summer. (We went to Stowe.) We brought our puppy, too! I’d love to visit Vermont in the fall sometime. Thanks for sharing!
I hope you enjoyed Vermont as much as we always do. We stayed in the Stowe area on our honeymoon in 1994 and returned there in 2017 and were shocked at how much that area had grown. It was still beautiful and we enjoyed visiting there.
Paula
As Liberty said above, your post was our most clicked this week! Congrats! I am not surprised because your photos are so beautiful! Once again, thanks for linking up and have a great weekend!
Shelley
Thank you, Shelley!
Paula
Thank you for taking us travelling with you Paula. What a picturesque and amazing place Vermont is. Your photos are gorgeous and I love that you take Sherman with you on your travels.
Thank you for sharing at Create, Bake, Grow & Gather this week.
Thank you, Kerryanne! We had a fabulous trip.
Paula
Each photo looked like a post card! I am definitely going next year! And how wonderful to be able to take Sherman! Thanks for posting these in your Pinterest Challenge this month!