Last week I had a belated birthday trip up to Vermont, which was on my Autumn Intentions list! I got some inspiration for my trip from, Mackenzie of Design Darling in this post here, but I also wanted to make the trip my own so I added some other fun activities to our two-day trip! I haven’t been to Vermont in what feels like forever, probably because it has been forever! This trip was incredible, more so than I could have imagined. I would 100% suggest taking this trip in October/November to my friends, my family, and YOU! Keep reading for all the trip details…

Thursday Morning- Wake up *super* early and drive to Manchester, VT

THE DRIVE: It’s a goooood 3.5hr drive from Greenwich, CT to Manchester, VT so we left bright and early on Thursday morning- I’m talking before 7am! We took the scenic route (honestly, just went the way Google maps took us), which took us up the Taconic Parkway and then on a bunch of windy back roads once we got into Vermont. I’d highly suggest our route as it was so relaxing and the fall foliage was incredible! It felt less like a boring drive and more like an exciting adventure!

THE BRUNCH: We thought about having brunch at The Equinox, but I was on the fence about whether I wanted to do a nice (and frankly, overpriced) breakfast or if I wanted to do something more homey. We opted for something casual at Up For Breakfast and were not disappointed! First off, it was really reasonably priced, they had an extensive menu that would please anyone, and the food was really good! I ordered off their daily specials menu and had a stack of pumpkin, walnut, blackberry pancakes. My boyfriend got the blueberry pancakes and we split a side of home fries! Make sure you get the home fries!

THE TOWN: Up For Breakfast is located right in the middle of Manchester’s tiny downtown, so we walked around a little before driving back to The Equinox. It was overcast and drizzling slightly so we cut our walk around downtown short and instead headed over to The Equinox (only about 5 min away) to check out the historic hotel. I considered staying at The Equinox when booking our trip, but opted for the Woodstock Inn instead since it was not only significantly cheaper, but also recently renovated! Yay! If you’re in Manchester, without a doubt you should make sure you stop at The Equinox to check it out! It’s really nice!

Thursday Afternoon- Head to Woodstock, VT for a mini “Makers and their Craft” Tour

THE DRIVE: From Manchester to Woodstock, it’ll take you 1.5 hours and again, it’s a really nice drive. You’ll pass countless country stores (none of which we stopped in and that’s one of the only things I wish we had done differently on our trip!) each having so much Vermont character and charm. Driving from Manchester to Woodstock you’ll pass by the town of Woodstock before the places we visited, so just keep that in mind if you want to swing by your inn to freshen up/regroup mid-day. Definitely take the time to stop by covered bridges as you pass them. Maybe it’s just me, but I like walking over them if they have a pedestrian pathway and of course, as a blogger, I love all the photo ops!

THE SIMON PEARCE FLAGSHIP STORE: Laugh all you want, but I have a special place in my heart for glass stores. Sweet Home Alabama is one of my all-time favorite movies and I love the scene where Reese Witherspoon walks through her ex-husband’s glass gallery/store and is blown away (pun intended) by how each piece of glass is a piece of art. So with all that being said…going to Simon Pearce was a no brainer! Funny enough, there’s a Simon Pearce store right at the top of Greenwich Ave, but obviously it’s not the same as going to the headquarters in Quechee, VT. In addition to browsing all of their glass products, we got to learn how to make handblown wine glasses! How cool! There is a restaurant and bar on sight, both look really nice and I wish we had time to dine/drink there, but oh well, next trip!

THE SUGARBUSH SUGAR FARM: No trip to Vermont is complete without getting some VT made maple syrup. Duh! I wanted to go to an actual sugar farm, where they tap the trees and turn the sap into maple syrup, and stumbled across the Sugarbush farm right outside of Woodstock. You have to drive over a covered bridge to get there (bonus!) and a couple miles of dirt roads, so just keep that in mind depending on your car. Sugarbush farm is really rural, they’ve got farm animals, and surprise- they also make cheese! Your visit will consist of exploring the farm, learning about the process to make maple syrup, sampling some cheese and syrup, and more! We left with some cheese and syrup, great gifts for our family back home!

THE COVERED BRIDGES: I already said this, but there are covered bridges everywhere! My favorite of them is right across the street from the Woodstock Inn. From the Woodstock Inn you can walk into the downtown area along with exploring along the river.

THE WOODSTOCK INN: We finally checked into the inn around 4:30pm, just in time for the end of tea and cookies hour. We didn’t love the cookies, but we did enjoy some tea and hot cocoa after a rainy day! It’s always a nice little bonus when hotels offer these sorts of things! I was blown away with how gorgeous the hotel lobby was! It was cozy, warm, homey, but also light and airy. You could tell they did a lot with renovations and lemme tell you, it paid off! In addition to the updated space, the inn was perfectly decorated for fall! From festive pumpkins and harvest decor to autumnal cocktails at the bar, the inn kind of felt like a Hallmark movie! (In a good way!)

THE ROOM: We stayed in one of the Woodstock King rooms, which are a decent size and have a luxurious bathroom (although the bathroom wasn’t large). Not only was the room spacious, it was very clean! (I have high standards.) Upon entering our room we noticed a really cute surprise — a Vermont cheese board with Vermont apple cider! How sweet!

Thursday Evening- Cocktails and Hot Tubs in Woodstock, VT

THE BAR: The Red Rooster, which is located centrally right off the lobby of the inn, had a great bar menu with fall themed cocktails. I loved my bourbon and hot apple cider drink, which I enjoyed much later in the evening, but kicked the night off with a glass of wine (which the bartended comped because it was my birthday, how sweet!). I liked the vibe of the bar too, there was a nice atmosphere, a good crowd, but still chill and relaxed.

THE ATHLETIC CLUB: Located off property about 1.5 miles away from the inn, the Woodstock Athletic Club hosts a fitness center, an indoor pool, hot tub, sauna/steam room, and lots of other amenities! I’m a huge fan of a hot tub, especially after the chilly, fall travel day that we had. It was so relaxing to just spend some time in the whirlpool before heading to dinner.

THE LOCAL SPOT: The inn recommended a few different places to eat dinner off property. The two options were The Price & The Pauper, which offers an upscale dining room requiring advanced reservations and also a bistro area, or Worthy Kitchen, a relaxed bar feel with healthy menu options. We went with Worthy Kitchen and are so glad we did! They had some great vegetarian options and it was such a fun atmosphere! On a Thursday night it was packed with locals, including one of the coaches of the undefeated Woodstock Union football team and his family. How cool?!

Friday Morning- Rise and Shine and Drive

THE DRIVE: Another early morning on the road! We left the inn a little before 7am to make the trip back down to Manchester. It was bittersweet, obviously it would have been nice to have a relaxing morning hanging in/around the Woodstock Inn, but we had to get back to Manchester for a really exciting outing! We took the same route back to Manchester that we’d driven the day before  passing the Calvin Coolidge historic home and lots of untouched Vermont countryside.

THE BREAKFAST SPOT: The Works is only a couple minutes away from The Equinox hotel. It was the perfect, grab & go spot. When traveling I prefer to stop at local places rather than chains like Starbucks. It’s nice to go to the local spots, do you agree? After trying their smoothie and bagels (by the way, the dairy free cream cheese was really good!), we headed to our Land Rover Driving Experience!

THE EXPERIENCE: I’ll start by saying, I’m doing a whole blog post about my Land Rover Driving Experience within the next week, so I won’t get into it much here, mostly because I don’t want to ruin the surprise and how amazing it was! I was so excited to partner with Land Rover Experience in Vermont and truly learned so much about how to drive my car off-road! It’s incredible what Land Rovers can do! I would highly recommend this experience to anyone, it was a really unique experience and nothing like I’d ever done before! Doing this experience in the fall with all the fall foliage was really beautiful!

THE DRIVE HOME: The drive home was much like our drive up to Vermont. However, we made a point of stopping at a road side diner in Chatham, NY off the Taconic Parkway. It’s literally in the middle of nowhere, but conveniently located right across from a gas station. The diner has that old timer charm and probably hadn’t been updated much since it was established in the 60’s. The food was great though! It was nice to get out of the car for a little bit, enjoy some pancakes and home fries, before heading back to hectic Greenwich. I’d highly suggest stopping here if you take the Taconic Parkway up to Vermont!