4 Fall Days in Woodstock Vermont

Sleepy Hollow Farm
Happy Wednesday loves! Hope you had a great weekend. We had a 3 day weekend which was SO nice and relaxing. The weather was also pretty nice especially on Monday so we fully took advantage since I think the temperatures are going to be dropping significantly over the next week.

Y'all where do I even begin? We absolutely fell in LOVE with Vermont--especially the town of Woodstock. It's one of those destinations I can see us visiting annually for a little couple's getaway and weekend to decompress. We did drive there and it really wasn't too bad. We do a lot of long (ish) road trips since I'm not the biggest fan of flying but if live very far away and have a Vermont getaway on your bucket list, I would recommend flying into either Boston or Albany! I personally think that Albany would be easier with less traffic in the surrounding area.

Day 1

We drove halfway on Wednesday night and finished the drive Thursday which put us arriving around lunch time. We immediately checked into our adorable Inn for the weekend called 506 On the River. It's such an adorable Inn with a very rustic/farmhouse vibe. If you're visiting, I HIGHLY recommend staying here. Our rooms were so cozy and right on the river which was very relaxing. They such a yummy country breakfast every morning and the coolest bar that was a very popular spot every night. It's only a 3-5 minute drive outside of the main downtown area so it's a perfect location and it's right next to an AWESOME farmer's market.

After we checked in, we immediately headed into the town and started exploring. One of our favorite shops in the downtown area is F.H. Gillingham & Sons. It's this adorable market/general store with tons of local food/wine/beer/etc. My two other favorite stores in the downtown area are the Yankee Bookshop (literally the cutest bookstore I've ever been in) and Clover (adorable candles/home decor/holiday trinkets/etc.). 

There were so many houses that were so incredibly dreamy especially with their fall porch decor. I could just wander around this town forever and never get tired o the charm.

The porch below  was definitely one of the most unique! Definitely inspiring me for next year. The fact that we arrived on Halloween day made it even more fun.

We had another hour or so to kill before our dinner reservation and the Woodstock Inn is right in the center of town so we decided to look around the grounds and also swing by the gift shop. This place is pretty gorgeous so next time we go we may end up staying here. It's a little pricey so we'll see!

Finally, it was time for dinner and we headed over to The Prince & The Pauper which is right in the little downtown area. This place was highly recommended on quite a few of the travel blogs I checked out before our trip. You do have to request reservations so if you want to dine here, I would recommend doing so about a week or so in advance. The dinner was AMAZING and it was a very romantic setting.
Coat, Sweater, Jeans, Scarf, Boots

Once we were done with dinner, we didn't want the night to end so we went to the bar at our hotel and it was a blast. Our bartender was super helpful and gave us a ton of recommendations for the rest of our trip!

Day 2
The next day (Friday) we hit the ground running. This was definitely the most jam-packed day of the trip. Even though we did a TON while we were there, it was all on our own timeline and it still felt very relaxing. 

We started off with coffee at Mon Vert Cafe in the downtown area. This is definitely a SUPER popular spot and next time we visit, we'll definitely try out their breakfast. It looked so yummy but since the breakfast at our Inn was awesome and free we decided to pass this trip. First stop was the Taftsville Covered Bridge which is one of the oldest in Vermont. It passes over a huge dam which was pretty neat. Pro tip: If you have your heart set on seeing the famous Sleepy Hollow Farm, definitely stop by the covered bridge first then you can take that road right to the farm. That's what we did and it worked out so well!

We drove up to Sleepy Hollow Farm (one of the most photographed New England farms) which is photographed in the first picture and again below. It was absolutely stunning and so worth the little drive! Apparently it's for sale right now. If you have 12 million it can be all yours!

After this, we decided to head to Quechee (only 10-15 minutes from Woodstock) to go to Simon Pearce. Simon Pearce sells beautiful handcrafted glassware and they also have an adorable restaurant that's right on a dam which makes for pretty incredible views. We had originally planned to do dinner there but I'm so glad we ended up going for lunch because we got to take in all the views. It was a super windy day so I didn't get a ton of pictures but just look at their website to get a feel for the amazing location! 

They temporarily closed their glass-blowing demonstrations but you could actually drive a few minutes to the next town where they have their Factory/Outlet store. This store still has the glass-blowing demos which Steven really enjoyed. The other great thing about this location is that it was right next to Harpoon Brewery which was next on our agenda anyway!
Coat, Sweater, Scarf, Jeans, Boots

While you're visiting I highly recommend stopping by the Artisans Park. Not only is it the home of the Harpoon Brewery but right next door is an adorable cheese shop and across the parking lot is a Preserves store (Blake Hill) that sells amazing jams/jellies. There's also a distillery that we didn't get a chance to check out.

While we were in Windsor, it was recommended that we drive by the Windsor Cornish Covered Bridge because it's actually the longest one in Vermont! This was cool to see but probably something you could skip if you're short on time.

At this point we were pretty exhausted so we decided to head back to the room to relax for a few hours. Our bartender had recommended Melaza as a good spot for dinner/tapas so that was our next stop. I LOVED the food here so I'm really glad we got this recommendation. If you go, definitely order the Sofritas. 

Day 3

We last minute decided on our third day to head up to Stowe. We mainly went because Steven wanted a specific type of beer from this brewery called Alchemist and I'm glad we decided to make the trip. Stowe is an adorable town and definitely has more of that "ski town" feel. We parked and walked around the main downtown area. There's a ton of cute "country stores" and "general stores" that carry a lot of local goodies. We grabbed coffee at Black Cap which I highly recommend. They made a really yummy chai latte and Steven got a maple latte. 

After walking around the downtown area a little more, we headed to Alchemist so Steven could pick up his beer and see the brewery. This was definitely the highlight of the trip for him and I will say that the brewery was really cool and in a gorgeous spot!

Further up the mountain, we decided to see the Trapp Family Lodge which I was VERY excited about. Sound of Music is one of my favorite movies of all time and this was such a neat experience...however, if you've been following for a while you may know that I have a pretty crippling fear of heights. Even though we weren't THAT high I went into full panic mode only a few minutes after walking around the lodge. These are the things you don't see on Instagram!

After that little episode, I felt like maybe I had too much caffeine and wanted to dilute it with some food. We stopped at this really cool pizza place called Piecasso which was conveniently located on our way back to the highway AND I saw that the lovely Biana had recommended it in her post (linked here). They had an AMAZING gluten-free pizza option so I'm really glad we stopped there.

As we made our way to the highway to venture back to Woodstock, we remembered passing an adorable cider mill on the way in and decided to swing by for our favorite food--cider donuts. This is definitely worth checking out and looked like a fun place to grab lunch!

At this point we were pretty tired so we hung out in our room for a bit but since it was our last night we weren't ready to call it a night just yet. We ventured over to Long Trail Brewery which is only 10ish minutes from our Inn. It was a really fun environment although as someone who doesn't like beer I was kind of disappointed in their options. Typically I'll get a cider or a sour of some kind because it's the only kind of beer I can manage to drink but unfortunately they were totally sold out of those. Regardless, it's a super fun place and if you like beer it's a must visit.

After this, we went back to the Inn and played some board games in their adorable library/billiard room. 

This was SUCH a fun trip for us and like I said before, I think that this may end up being an annual destination. We loved Vermont so much and would love to explore Burlington while we're up there next. I will say that I don't see myself actually lodging anywhere but Woodstock because it was the most charming town EVER! Highly recommend to anyone planning a New England visit. If you want to see foliage, definitely plan to go earlier in October as we didn't see a ton while we were there but it was still gorgeous regardless.

Hope y'all enjoyed this post!

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  1. How beautiful! I want to go there! These photos are absolutely stunning and it looks like a place that is completely filled with romantic vibes for a couples getaway! I love that they have a tiny little independently owned book shop. Those seem to be so obsolete these days, it makes me sad. We don’t even have a large bookstore where I live. The closest one is over an hour away.


  2. The place is amazing! <3 Looks like a painting from a book. Must be a beautiful experiences to life there. :)

  3. For as long as I've lived in Boston we have never been to Woodstock and it's so picturesque!! I love all the fall foliage - it's perfect! So glad you guys had a great time! xo, Biana -BlovedBoston

  4. Oh wow! Thanks for the feature! It made my day! I've been to Woodstock so this post brought back a lot of memories for me. Such a beautiful town!

  5. Such beautiful pictures and loving your outfit!
    Ellibelle's Corner

  6. Looks like a charming weekend. Thanks for linking up with us!

  7. Vermont has been on my bucket list for years. And this post is exactly why!! What a beautiful place to visit and there could not be a better place to experience all the fall vibes!!


  8. Talk about fall perfection! Your pics are sooo stunning, lady!

    Le Stylo Rouge

  9. Quintessential New England Fall! Such gorgeous photos, you captured everything beautifully!

    xx, Elise

  10. How cute is that book shop! I've been wanting to see Vermont in the fall for a while, probably next year xx

    Stylish + Faux Fur Vegan Winter Coats | Vegan Fashion + Lifestyle Blog

  11. What a quaint town! It looks amazing and your photos are beautiful! My daughter is going to school on the east coast and this would be a perfect family weekend getaway!

    Jill - Doused in Pink

  12. These are really cool spots dear! Lovely snaps you have here.

    Jessica |

  13. Wooow! Nice place dear!! You had a great time!
    Have a lovely day! xx

    La ilusión de Nina -

  14. Wow, it is so charming!! These photos are just so amazing!

    Amy Ann
    Straight A Style