A Perfect Fall Weekend in Vermont
Nothing quite screams quintessential fall like quaint New England towns. Vermont in particular comes alive with color and charm during the fall seasons of September through November. The perfect weekend spent there often includes the crisp air, beautiful foliage, and activities such as apple picking, hiking, trying maple syrup, and enjoying a beverage by the fire. Read below if you’re ready to learn the ins and outs of planning a fall weekend in Vermont.
When to Visit?
Predicting when the leaves will be in peak bloom is nearly impossible, but there are ways to make the best educated guess. Generally, the best time to visit mid-vermont is the first week of October, and it varies how far north or south you are planning to stay. This time is much earlier than New York City (late October-early November) due to the colder climate. This foliage forecaster helps to predict by region after inputting email, and is a good judge of the foliage per week. Additionally, this website gives a general map per month of the foliage.
Tip: If visiting Woodstock (spoiler alert for this blog), it’s important to make restaurant reservations ahead of time. Being one of the biggest tourist attractions in Vermont, finding a nice place to eat on a weekend will be tough doing walk-ins.
Getting to Vermont
There is no other great way to get to Vermont than driving. From NYC, to fly there would need to be a layover in Boston airport and would take much more time than driving. When in Vermont, the best way to get around the picturesque towns and activities is driving as well.
Where to stay
A good mid-way point and cute town that is near many fall activities is Ludlow, VT. When I stayed there I found cute restaurants and shops, beautiful landscapes, and accessibility to what I wanted to do. I stayed in an Airbnb there with friends, but the Main and Mountain Bar and Motel offers affordable rooms in the center of town. What makes this town popular is Okemo Mountain Resort resides in this town and attracts thousands of people during ski season, so the main street is built up compared to other smaller Vermont towns. There are plenty of towns to stay in, you can’t really go wrong!
Friday: Settling into town
Dinner in town: After traveling from the surrounding area to get to Vermont, enjoying a nice meal is top of mind. If you want more fine dining, try The Downtown Grocery. If looking for something more casual, Goodman’s American pie is a family favorite or picking up at Tacos Tacos.
Night time drinks: End the night by the outdoor firepit and cocktail at Main and Mountain Bar. The craft cocktails are fun and the ambiance is even better!
Saturday: Full Day of Activities
Apple picking: Wellwood orchards
Wellwood Orchards became one of my favorite places to pick apples (link here)! About a 20 minute drive west of Ludlow, Wellwood is an orchard where you can pick your own apples. Upon arrival, there is a market to purchase hot apple cider and fresh apple cider donuts being made right in front of you! If you didnt eat breakfast yet, those donuts really hit the spot (I was addicted). The market also includes kits to make caramel apples, apple crumble, and homemade, creative jams to take home. After a hay ride takes you right to the orchard, you have a designated bag to choose from an array of different types of apples. Make sure to take lots of pictures because the landscape is beautiful on a sunny day.
Brewery: harpoon brewery
If you are a brewery lover like me, Harpoon Brewery nearby is always a hit. They had outdoor picnic tables that had lunch options, beer flights, ciders, and live music on weekends. They specialize in different types of fall beers and is a lot of fun to try with friends! The brewery has cornhole and other outdoor activities that are fun for all ages.
Woodstock
An autumnl Vermont weekend wouldn’t be complete without a trip to Woodstock- think: Gilmore Girls or any Hallmark small town movie set. This town is full of charm and the residents participate in festivities decorating their houses. The Central Street in Woodstock is home to general stores, book shops, cafes, clothing stores, in the most aesthetic way possible. F. H. Gilligham & Sons is the cutest general store in the middle of town to buy fun gifts for family and friends. The Vermont Flannel Co. is the perfect spot to pick up a cute outfit in case you had nothing New England-esque this weekend. To end your day in Woodstock, make a reservation at the Prince and the Pauper restaurant: everyone can find something they like!
Picture spots in Woodstock:
One of the most iconic photo-ops in the area is Sleepy Hollow farm (real address 3429 Cloudland Road, Pomfret, VT) and is recognizable worldwide. Cars line up for up to a mile down the road to take some pictures of this beautiful scene. However, make sure to look up the status of the farm- there are rumors residents want to shut down the street due to noisy tourism.
The famous Vermont Covered bridges do not fall short in Woodstock. Right off the main strip in town is the Middle Covered Bridge (link), a beautiful spot to take a photo. Yes, it is a real-working bridge and there are cars that go over it so be careful! I did risk my life to take a photo in front of it, but ya gotta risk it for the biscuit.
Sunday: Hike and Home
Breakfast and Coffee
Breakfast is the most important meal of the day, right? (I don’t actually believe this, but let’s not get into it). After checking out of your hotel/Airbnb, head over to Cafe at De Light or the Hatchery for an all-american breakfast. If you’re more of a grab-and-go, boutique coffee only type of person, head over to TPW Coffee bar for a speciality drink.
Hike
There are hikes for all skill levels in this area. For me, an inexperienced hiker who happens to also be clumsy, opted for the drive mostly up Okemo mountain and hike-as-you-please. The scenic drive up the mountain was covered with changing leaves, leave your window open for the actual scent of fall.. Sorry Starbucks. You can park your car in one of the scenic lookouts to hike around and discover some trails. The view at the top is breathtaking and definitely worth going all the way up to.
For other trails in the area, visit All Trails.
Stop & Shop
On your way home, don’t forget to stop at the Vermont Country Store in Weston. This place is incredible, basically Vermont encapsulated in a store. There are different varieties of Maple Syrup to take home, from light, to amber, to eventually dark. Food, clothes, games, basically a one-stop-shop to buy things before leaving the state. Across the street is the Weston Village Christmas shop. I know this is an autumn article, but if you’re a Christmas ornament fanatic like myself it can’t be missed before going back home.
