Fall in Vermont: A Trip Guide

Though Vermont glitters under a white blanket in the winter and blooms shocking green in the spring and summer, the most famous season of all is definitely FALL. September and October bring in a fiery transformation that streaks across this state’s many trees. 

Fall in Vermont

But it’s not just pretty. The harvest season also means a lot of activity. Farms, orchards, wineries, breweries, hay rides and more are all underway. And yes, as I visited during the 2020 pandemic, there was less open than usual, but Vermont has always been about the outdoors, so many of my favorite activities are still happening in some capacity.

 

I was in need of a little fall country fun and was delighted to spend a week exploring the autumn bounty in the Northwestern area of Vermont. This region has glittering lake views, sweeping hillsides and picture perfect farms, scattered along it’s breathtaking roads. Adventuring with my 2 year old daughter, we had the most memorable week frolicking throughout the countryside and embracing everything FALL. 

 

When to go?

Last week in Sept – First 2 weeks in October

Peak fall in Vermont usually occurs at the end of September and early October. You might catch some golden leaves in mid September as well. Don’t wait too long in October though! By Halloween, there’s usually been some frost and the leaves lose their vibrancy or most have indeed, fallen. 

 

Where to Visit?

Vermont in the fall

I grew up in Woodstock, which is Eastern central Vermont. The fall in Woodstock is stunning and there is an adorable town to go along with it. But I think the most scenic countryside is along route 7 in Northwestern Vermont. Here you have quiet roads, farm stands and majestic mountains, all set on the backdrop of Lake Champlain, just a couple miles West. It has a full fall experience, all within 20 minutes. 

 

Where to Stay?

Basin Harbor 

Breakfast in our cottage at Basin Harbor

There’s no doubt that Basin Harbor is where to stay if you want to experience the best of Vermont. Quiet renovated cottages perched next to the dazzling Lake Champlain, a historic lodge that serves everything from waffles to sushi and an assortment of adirondack chairs thoughtfully placed with views. The peacefulness that Basin Harbor brings allows guests to breathe in the autumn air and fully immerse in Vermont’s natural splendor.

Basin Harbor’s iconic adirondack chairs

Don’t even bother with your car, use a golf cart to get around this massive resort, from the general store to the pool to the Red Mill restaurant. If you have had your fill of all that lake gazing and cozy fires, there’s actually a lot available for the adventure seekers too. 

Get around by golf cart at Basin Harbor

 

What to do?

Cruise the Lake at Basin Harbor

Boat cruise on Lake Champlain

Many leaf peepers take in the foliage by car or on foot, but I daresay that viewing it from a boat might be the most picturesque. Lake Champlain, Vermont’s largest and in my opinion, most gorgeous lake, is hugged by rolling hills, making it an autumn lovers dream. Basin Harbor offers daily cruising aboard it’s EScape, a 47’ modified lobster boat that can seat up to 48 people (modified capacity during COVID-19). The tour will include the centuries old history of the Basin Harbor and Lake Champlain, as well as highlight more scenic spots along the lake.

Daily narrated cruises on the EScape from Basin Harbor

 

Craving something with a little more speed? Rent a boat to do some tubing or waterskiing, or take out a motor boat with just your family if you prefer to have a more socially distant experience. The calm water and reflection of those leaves will definitely ensure that you have stunning photos!

The eagle’s nest

 

Apple Picking at Happy Valley Orchard

A quintessential fall experience, apple picking is one of those things that is just fun (and easy) for all ages. Great photos, lovely outdoor orchards and using a lot of tasty bites along the way. My toddler loved learning how to twist and pull off the apples on the low branches all by herself.

Apple picking at Happy Valley Orchard

We were told by a local about Happy Valley Orchard in Middlebury (about 35 minutes south of Basin Harbor) and it was perfect.  This cute family orchard has well maintained trees, which were simply full of apples. If you don’t feel like picking, the market has bags to carry out, including the beloved Honeycrisp, and other local specialties. It’d be a tragedy if you didn’t snag a bag of cider donuts to share (or not!). 

 

Pick a Pumpkin: Lester Farm Market

I daresay there’s a place in the country that has prettier pumpkins than Vermont. These beauties are for sale along the side of the road, at local farms and markets everywhere during this time of year. However, I have to give credit to Lester Farm Market.

Lester Farm Market is A+

Their thoughtful display is out of an foliage postcard. Wagons piled high, pumpkin “spiders,” and a pumpkin adorned house big enough to enter;  their market offers so much more than just picking out a pumpkin!  The photo opportunities alone are worth the price of these orange icons. 

 

Eat Well

Pizza and beer are a winning combo, any time of the year. The local favorite, Folino’s Pizza, is a laidback stop for some great slices, and next door, sample a refreshing beer from Fiddlehead Brewery. 

Lunch with a lake view from Mizuchi Sushi at Basin Harbor

If you want some more unique flavors for this area, Mizuchi Sushi is a new offering from Basin Harbor. These exciting rolls and other Japanese dishes from New York Times rated veteran chef Fumitaka Takeshita are absolutely delicious, on their own but I think they are greatly enhanced by enjoying them with a view of the lake. 

 

Hang out at The Historic Marble Works District, Middlebury

The collegiate Middlebury is a charming town, centered around a breathtaking waterfall. Though the town feels very historic, it is also very lively. A particularly fun and innovative spot is the Marble Works District.

Marble Works District, Middlebury, VT

Here you will find a park with picnic benches, art installations, gardens and a prime waterfall view. Bring a meal or some wine, or just stop by to enjoy the fall sunshine. Even better, there are cute shops to browse and the Vermont staple, American Flatbread, which serves outstanding pizza, salads and drinks either outside by a firepit, inside in non-pandemic times or to go!

 

Immerse in Nature on a Hike

Crunching on the crispy leaves as you walk along the Vermont trails is truly spectacular. Get in nature and leave your phones behind. Breathe in the rich air, hear the rustling of birds and let yourself be a part of the Vermont landscape.

A scenic “hike” (walk) with a toddler

 

Learn about local farming at Shelburne Farms

One of the most exquisite farms in all of the state, Shelburne Farms not only provides a beautiful way to experience farm life, including a wagon ride, but they also serve lunch, make their own cheeses (which you can purchase) and even have an inn. During the pandemic, much is closed, save for their hiking trails but if you plan to go at other times, don’t miss their friendly cows, baby chicks and excellent cheeses from their market!

Shelburne Farms wagon ride up to the barns

 

Some of my favorite moments of our week in this beautiful area of Vermont were spontaneous. We pulled over on the side of the road to take a photo of a cow near a fence or drove along old winding roads to be surprised by a stunning valley of red leaves or wandering the quaint town of Vergennes to find a delightful shop with toys and home goods (Malabar). There’s as much or as little to do as you want. And all the while, it was easy to be present in this gorgeously fleeting season, relishing every moment of its beauty while it lasts.

Two happy girls in Vermont’s Fall

Winter in Vermont at the Woodstock Inn and Resort

Each time I go back to my little Vermont hometown, I am reminded that I basically grew up in a storybook. Woodstock, Vermont is a bucolic little village nestled amidst rolling hills, hugging a charming center green and a briskly flowing river.  Stone, brick and cape houses line the ambling streets that make up this 3000 person town, every bend of it steeped in time.

The Woodstock Covered Bridge

The Woodstock Covered Bridge

It’s no surprise that my fellow New Englanders know of Woodstock, VT. I’d even say, many beyond the Northeast are aware of this popular weekend hideaway. For such a small town, its reputation precedes itself — and for good reason.

The hectic, digital day-to-day stresses are buried beneath the quiet splendor of village strolls, breathtaking hikes up Mount Tom or afternoons spent skipping rocks along the river.

Though you do get cell service here now (we didn’t when I was growing up), you just might want to turn off your phone and enjoy the rare and simple pleasures of this place.

When asked about Woodstock, the one word that usually comes to my mind is “quaint.” But don’t get my wrong,  that doesn’t mean it is boring! There’s a lot of energy in this 350 year old town, and every time I return, I see that energy increasing. I’d attribute a lot of that forward progress to the town’s centerpiece, the Woodstock Inn and Resort. (My father runs his jewelry shop in the heart of town, and has for the last 30 years, and he definitely agrees that the Inn is a huge factor in keeping Woodstock so relevant.)

Gillingham’s, the town general store

Some iteration of the Woodstock Inn & Resort has been welcoming guests for 225 years.That is crazy! I’ve traveled all over the world, filming some of the world’s best hotels, and that type of hotel history very is RARE, especially in the USA.

The Inn started out as a small bed & breakfast, and over the centuries continued to expand and gain more and more popularity. In the mid 1900s, Laurance Rockefeller, a former resident of Woodstock, bought the hotel and it was under his leadership for 50 years. He definitely helped to put it on the luxury hotel map, in a big way.

I am very fortunate to have had such a legendary resort in my hometown backyard. It has been part of my family’s story forever, playing host to special dinners, celebratory breakfasts, parties and even prom!

Woodstock Inn during Christmas

It was such a treat to return to the Inn just after Christmas and share this special hotel with my daughter, Aurora. I look for different things in hotels now that I am a mom and I have to say, the Woodstock Inn & Resort surprised me with being exceptionally family friendly. They had undergone expansive improvements when I filmed the property in 2013 for my Get Lost in Woodstock series but now, they’ve added even more luxurious detail to all the public areas and the guest rooms in particular. 

 

Fireside Ambiance

Fireplace at the Woodstock Inn

Fireplace at the Woodstock Inn

Ever since I was a little kid, I was drawn to the oversized fireplace that greets you as walk through the Inn’s entrance. The cozy feeling with the couches and sitting areas, beautiful wall color and attention to detail, makes the entire main area of the Inn so welcoming. I wanted to sit in on each sofa and relax with a cup of tea (you can actually do that during their daily afternoon tea time). We of course didn’t have spare moments for that with a 6 month old, but it was fun to daydream about as I hurriedly walked past these lovely areas with my tired/hungry/active baby. 

 

Legacy Suites

Having a little one with a strict bedtime of 7pm complicates hotel life a bit for us parents. After 7pm, it is lights out (and complete silence) so having an additional room is more than necessary. We absolutely loved the newly renovated Legacy Suite. Ours in particular was the Frederick Billings Suite, the legendary local that was a pioneer in the farm industry and a famous face in Woodstock. It was situated in the main part of the inn and had tasteful decor that highlighted Vermont’s farm history. 

Woodstock Inn & Resort

As you enter, there’s a long tiled hallway to the bedroom and adjoining sitting room. (You can see a walkthrough on my Instagram stories here) I loved how the suite was situated far from the door, with the bedroom set back against a lovely view of the Inn’s snowy backyard. This distance made the whole suite feel more private and like our own apartment as opposed to a hotel room.

Frederick Billings Legacy Suite

The stone bathroom and rain shower with Zents products was modern and chic. The separate sitting room was decorated in rich hues and woods, making it feel like a cozy study. Though it had a wet bar, TV and pull out couch, this room became our daughter, Aurora’s room. The Inn provided a crib and we set up her changing area and toys in here. It was perfect! She happily napped here throughout the day and fell asleep at 7pm each night, and mom & dad could close the door and relax.

We were even able to order room service and hang out for a few more hours with my parents while Aurora happily dozed next door. This is a parents’ dream! We had the best of the Inn’s dining and didn’t have to disrupt our daughter’s sleep. 

Room Service dinner with the parents!

 

Red Rooster

Breakfast at the Red Rooster

What a delicious way to start the day! My parents met us here at The Red Rooster for breakfast and we all followed our noses to the two rooms filled with a sumptuous breakfast buffet. Fresh fruits, made-to-order omelets, a variety of homemade pastries and specially crafted breakfast treats awaited our empty plates. I was especially excited to see the giant, serve yourself maple syrup stand! (As a Vermonter, it runs in my veins of course 😉 

VT SYRUP! YES PLEASE!


Happiest Hour

A favorite of my parents’ for decades, Richardson’s Tavern has not lost any of its signature warm ambiance. The dimly lit room is where you want to be to unwind fireside after a wintery day, holding a drink and enjoying pub style bite.

Red Rooster Cocktail Bar

Red Rooster Cocktail Bar

I also was impressed by the newer bar at the Red Rooster. A brighter version of the tavern, the bartender makes excellent cocktails here and I loved the elegant style of this space and its marble bar.

 

Retro Game Room

Game Room at the Woodstock Inn

Retro Game Room at the Woodstock Inn

Even in the game room, the Inn retains its personality here. This classy area showcased working vintage pinball machines and a long wooden shuffleboard table. There was a pool table, a fireplace and more–no wonder it was packed! These games might have been out of Aurora’s age range, but hey, they sure entertained her competitive parents very well.

 

Woodstock Athletic Club

I am very familiar with the Woodstock Inn’s Athletic Club as I used to be a part of the Woodstock’s high school tennis team and these were our home courts. All guests of the Inn have free access to the pool, gym, tennis courts and workout classes. We opted to take a dip in the pool as Aurora finds pool time SUPER exciting. I think she thinks we are all taking a big bath with her. We splashed around and enjoyed ourselves for a morning.

 

Suicide Six Ski Area

We left Aurora with her grandma and myself, my husband and my dad hit the slopes of Suicide Six! My first time of skis was on this bunny hill and I spent too many afternoons and weekends skiing all these trails with my dad and friends throughout the years.

Located just 15 minutes from the Inn, this mountain is perfect for those that are into a fun, laidback day on the slopes. A brand new quad eliminated any lines for us and their snowmaking and grooming made for excellent conditions on the trails that were open.

Skiing with my dad at Suicide Six, like I did as kid!

By no means is this a large mountain, but its trails are beautifully cut through the forest (I even saw animal tracks as I skiied down). The classic lodge makes you feel like you are back in time and reminded me that this is one of the oldest ski areas in the country.

 

Billings Farm & Museum

Aurora did join us for a tour of Woodstock’s signature Billings Farm & Museum. It was so nice that the Woodstock Inn provides all guests with free entry to this unique local historical site and working dairy farm.

We did a self guided tour of the stables, the goat shed, chicken coop and cow barn. DO NOT MISS THE BABY COW NURSERY. It might be one of the cutest, up close experiences I’ve ever had baby animals. The baby cows were unbelievably friendly and social–they kept licking Aurora and nibbling on my clothes. She (and I) was shrieking with delight!

We were fortunate to make the talk about cows with a farmer in the dairy barn. Aurora’s eyes widened as she viewed her first full grown cow. The farmer on site gave us a lot of amazing information about these cows, how Billings Farm cares for them, their breeding, and their personalities! Aurora and I even got to brush one! 

It was with a heavy heart that we checked out and had to bid farewell to Woodstock. However, just like it has been throughout my life, the Woodstock Inn & Resort was the perfect backdrop to so many special memories with my parents, my husband and especially, our daughter.

I still cannot speak more highly of this resort’s appreciation for its out-of-towners as well as its locals. 

There’s something about the energy of this hotel that just brings about the most joyful times, no matter what time of year.

On our next visit, Aurora will be walking (!) and I am sure that we will have a whole different story to tell! Hopefully, more baby cows and maple syrup will be included.