Stowe vs Woodstock: Which Vermont Town is Better in the Fall

Table Rock New Hampshire

So you’ve decided pumpkin spice latte’s and your local pumpkin farm just isn’t quite “fall core” enough for you, so you’re heading to the epicenter – the ultimate embodiment of fall: Vermont. If you’ve got limited time and have to pick between two of the most magical towns, which should you visit? Let me help you decide. Woodstock vs Stowe, which Vermont town is better?

Stowe Vermont church

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I spent a magical 3 weeks literally zigzagging back and forth from upstate New York, across Vermont and New Hampshire, to Maine and back again chasing the best fall colors as they progressed farther south. I checked out as many highlights as I could as well as off the beaten path, less popular sights. 

Lake Wiloughby Vermont

Lake Wiloughby, Vermont

Many people consider Stowe and Woodstock to be two of the most quaint and charming towns in Vermont, or maybe all of New England. They wouldn’t be wrong! The towns are pretty adorable and magical, like something out of a fairy tale. 

Stowe vs Woodstock? What’s the Difference? 

When you compare the population of Stowe vs Woodstock, according to Google, Stowe has a population of just over 5,000. Woodstock has a population of around 3000 (these numbers seem to vary based on how one defines the town limits). To me, the downtown area of Stowe definitely feels much SMALLER with fewer shops and businesses in the town center that you may have seen in pictures. But much of the city and population is spread out so there are a number of restaurants and businesses you don’t immediately see that aren’t part of the famous main street. Woodstock feels larger on first impression because there seems to be more streets and area that includes the main downtown.

Stowe Vermont

Stowe, Vermont

The aesthetic is different too when you compare Stowe vs Woodstock. Stowe homes feel more Victorian while Woodstock’s seem more Federal or Georgian with red brick buildings. Stowe has a more whimsical view of the church and small downtown whereas Woodstock is more livable and charming, in my opinion, with compact streets that seem closer to the downtown. The entirety of Stowe is rather spread out, requiring some driving to see the entire town. The only part of town you’d really want to walk around is the picturesque main street with the white church. It’s rather small and can be seen quickly. Woodstock, on the other hand, although smaller in population and area, is more compact and walkable, with more historic buildings and homes.

downtown Woodstock Vermont

Woodstock, Vermont


History of Stowe and Woodstock, Vermont

Stowe got it start with its first settlers in the 1790’s. Agriculture and timber, as well as sheep and dairy farming dominated the early industries. By the mid 1800’s, Stowe had became a summer resort destination and in the early 1900’s skiing was introduced by Swedish families, kicking off Stowe’s notoriety as a winter vacation destination and some of the earliest alpine skiing in Vermont.

Stowe Vermont from a distance

Stowe, Vermont

Woodstock’s story began in the 1760’s as a hub for craftsmen, entrepreneurs, and artisans and they honor that history today as a tourist destination with a strong emphasis on local tradesmen and artisans. Soon, it was one of the largest towns in the state. The population dwindled in the 1800’s with the arrival of large factories but the railway coming through helped reconnect it to larger hubs and increase tourism.

Things to do Around Stowe

Stowe is very popular and in the fall, it can literally get so busy that there is a line of traffic going in and out of town all day long that stretches for miles. Parking in the tiny town is extremely difficult. I recommend driving into town either very early (especially if you plan to park) or quite late to avoid this line. 

1: Visit Historic Waterbury

The neighboring town of Waterbury is about 15 minutes drive (without traffic). It’s definitely cute and quaint and worth a short visit, even just for an hour or two.

2. Visit a Sugar Farm

Vermont is famous for its maple products. Therefore, if you didn’t go to a maple farm, did you really go to Vermont? (I didn’t go to a maple farm, shhh, don’t tell anyone). There are a ton of maple sugar farms to visit in the area like Nebraska Knoll Sugar Farm, Stowe Maple Products, Trapp Family Lodge, or Bragg Farm Sugar House.

If you’re like me and you just don’t make a maple farm tour a priority, especially since it’s not maple season in the fall, you can buy all the maple products your heart desires at these or other farms and pretty much everywhere in Vermont. These are SOOOO good!

Maple Candy

3: Ben and Jerry’s Factory and Graveyard

Just outside Waterbury on the way to Stowe is Ben and Jerry’s only factory open to the public. Here, you can take a guided tour and have some ice cream. You can also walk through the “graveyard” where you can see headstones and the stories behind some retired flavors. Check the hours before visiting if a tour is important to you. Also, be prepared for long lines if you visit in peak season like the fall.

Ben and Jerrys Graveyard Vermont

4: Cold Hollow Cider Mill

Cold Hollow is between Stowe and Waterbury and gets CRAZY busy in the fall. They are famous for their cider donuts (which I thought were overrated), maple creamies (incredible maple ice cream that you must have in Vermont), and all the maple products if you want to stock up. But the crowds are truly legendary. So come early on a weekday in the fall.

5: Percy Corn Maze

If a corn maze is on your list, this one is 5 minutes outside of Stowe, the owners are really nice, the setting is quite pretty, and it’s hard! The cost was $8 per person and leashed dogs were welcome. Chris and I literally had to cheat and push through some corn stalks to get out. After about an hour of miserably hitting dead ends, we just couldn’t take it anymore. But it’s dog friendly which is awesome!

6: Nichol’s Ledge

Somehow I totally missed this hike. I think we were just so busy, I lost track of some places on my list until after I’d passed them. But this hike has great reviews, beautiful views of Nichol’s Pond, and is an easy 0.6 mile each way. Because of falcon habitat, this hike is closed between March and August 1st. The trailhead is about 45 minutes drive from Stowe.

7: Smuggler’s Notch State Park

Just 15 minutes outside of Stowe, this state park is a pass through the Green Mountains. It is a notoriously windy and narrow road that closes in the winter. “The Notch” has historical significance as a route for illegal trade with Canada during an embargo in the 1800’s to fugitive slaves escaping to Canada and later during the prohibition era.

The highway 108, which connects Stowe to Cambridge, Vermont closes the 3.5 mile stretch between Stowe Mountain and Smuggler’s Notch Resort from mid October till May. This beautiful corridor is so narrow and windy, it cannot accommodate a vehicle larger than 40 feet according to state law. Every year, a number of long trucks get fined for ignoring and attempting to drive through and getting stuck across the road.

Aside from a campground and visitor center, visitors can go on hikes, rock climb, bike ride, picnic, and explore caves and waterfalls like Bingham Falls. Day use cost for the state park is $5 and camping is extra.

8: Go Out to Eat

Some popular restaurants are Harrisons Restaurant, Cork, or Plate for dinner and Butler’s Pantry for breakfast.

Where to Stay in Stowe, Vermont

Green Mountain Inn – It doesn’t get more quaint than this. For historic charm and magic during any season, this hotel right in downtown will probably be hard to beat. Plus, they have a pool, jacuzzi, sauna, and gym.

Field Guide Lodge – For something more modern and still close to town.

Goldilocks Cabin – If you’re looking for more space for the entire family and perhaps something quirky, unique and rustic, look no farther.

Tälta Lodge – For more of a destination lodge out of town and on the way to the ski resort, consider this well appointment modern property.

Good alternatives include The Little River Inn and the Grey Fox Inn.

Things to do Around Woodstock

Woodstock can get incredibly busy as well but parking seems to be a bit more plentiful than in Stowe, although traffic is crazy and you may have to drive around for a while to find a spot. Definitely try to arrive in the morning before 10 to have the easiest chance. 

1: Visit a Sugar Farm

Consider either Sugarbush Farm or Bourdon Maple FarmBoth are only minutes outside of town.

2. Go to the Market on the Green

Right in the heart of town in the park from 3-6 pm is the Woodstock Market on the Green every Wednesday from June 5th through October 16th. There are over 30 local vendors with local dairy products, produce, baked goods, live music, crafts, and activities.

3. Get a Maple Creemee from Woodstock Scoops

Grass-fed dairy ice cream made from local Vermont maple syrup (Bourdon Maple Farm) is simply delicious. And the maple creemees are soooooo, well, creamy.

Maple Creemie Woodstock

Woodstock Scoops

5. Billings Farm and Museum

Billings Farm and Museum is owned by the non-profit educational institution, Woodstock Foundation Inc. The impressive farm recently celebrated its 150 year anniversary of being a dairy farm. The farm attracts thousands of visitors each year, has educational exhibits, programs for the whole family, and showcases Vermont’s rural heritage.

You can learn more about the farm and their schedule of events HERE. There are plenty more historical sites to see around Woodstock if that is your thing.

6. Visit the Middle Covered Bridge

Ok, maybe this isn’t something you have to do, but the covered wooden truss bridges that cross rivers in Vermont are quaint and historical and there are more per square mile in Vermont than anywhere else in the US. One hundred years ago, there were over 600 covered bridges of this type, today there are just over 100 left in Vermont. The purpose of being covered was to protect the bridge from the weather and prevent decay and rotting. Many were replaced with steel. Their old traditional wooden structures epitomize the charm and era from which they were built, the mid to late 1800’s.

Middle Bridge is located on Mountain Avenue in Woodstock and is one of the most photographed landmarks in Woodstock, if not the whole state. The bridge was built in traditional methods in 1969 using wooden pegs instead of nails and had to be repaired after a fire in 1974. It can be driven or walked through. The pictured bridge below is not Middle Bridge.

Vermont covered bridge

8: Go out to Eat

There are a number of cute restaurants around and in Woodstock, Vermont. Some to check out are Mont Vert, Sante,The Prince and the Pauper, and Soulfully Good for breakfast or lunch.

If you’re willing to drive about 15 to 20 minutes, head to the Hartland Diner for breakfast. It’s unique and quirky, and perhaps a little politically triggering if you’re polarized. They have limited hours so check the schedule.

9. DON’T Drive by Sleepy Hollow Farm

Ok, so I’m adding this section purely to tell you you can no longer drive by or stop and take pictures of the famous Sleepy Hollow Farm. And rightfully so. They’ve closed the road for visitors. But I feel like I’d be leaving out a popular spot if I didn’t mention it. Coined “Sleepy Hollow Farm,” this private home is a picture perfect farm on a picture perfect dirt road a few miles outside of Woodstock. It became popular for photographers in the last decade or two and now, at all hours of the day from dawn till dusk, there could be dozens of cars lined up along the road, people setting up tripods in front of the house, people trespassing by running partway down the driveway, etc.

Sleepy Hollow Farm Vermont

Frankly, it’s incredibly awkward and I felt super cringey stopping there to take a picture. The road and barn are lovely, but I honestly think it’s overrated. So finally they’ve made it a private road this year.

One more fact, the farm was owned by Aerosmith guitarist, Joe Perry and his wife for a number of years until 2020.

Sleepy hollow farm

Where to Stay in Woodstock VT

Woodstock Inn – Definitely the most iconic in town, the Woodstock Inn is historic and charming and perfectly located to walk around town.

Woodstock Inn and Resort

Woodstocker B&B – An old historic farmhouse turned B&B, the reviews are excellent and there is a ton of charm in their 9 bedrooms.

Jackson House Inn – Also a historic and charming home, the Jackson House Inn was built in 1890, is in a beautiful setting, and offers a farm to table breakfast. They are also committed to eco-friendly practices.

The Village Inn – Also not lacking in charm, this historic inn also offers breakfast but has a tavern onsite. The reviews and location are excellent.

So…Which one is Better? Stowe or Woodstock

Everyone will tend to have their own favorite, but if I could only pick one, I’d pick Woodstock. There was more to see in town within walking distance, more close restaurants, and the homes are more aesthetic and interesting to walk or drive around and look at. People who live in Woodstock seem totally invested in the Halloween aesthetic! There are pumpkins and decorations everywhere in the fall!

Woodstock shopping

Woodstock Halloween

But the good news is, you don’t really have to pick between Stowe vs Woodstock because they are only a little over an hour apart. Why not visit both? One to three days in each is sufficient to see and appreciate the town. There is quite a bit to do in the vicinity around Stowe so maybe spend 2 or 3 days there first then head south to Woodstock for a couple more days.

Other Things to do Near Stowe and Woodstock Vermont

A few places that should be on your list of adventures that are not too far to drive to:

Franconian Notch Train tracks

Franconian Notch, White Mountains, Echo Lake, Flume Gorge, Artist’s Bluff, and the Frankenstein Trestle. And maybe this is weird, but I had a total fascination with cemeteries in New England. They are so beautiful and historic. With the fall colors, I couldn’t get enough. If you need a quiet place to get away from crowds (respectfully), this is it.

And not to throw another kink into your plans, but Montpelier, the capital of Vermont, is on your way between Stowe and Woodstock. It is also work a visit. The capital building is really lovely. And Burlington is a very hip and fun city to visit, go shopping, and check out some coffeeshops. I could go on and on, there really are so many things to see in Vermont and New Hampshire.

I hope this post helps you decide, which is better: Stowe vs Woodstock and which Vermont town you should visit this fall or falls to come!

Stowe vs Woodstock which Vermont town is better

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7 thoughts on “Stowe vs Woodstock: Which Vermont Town is Better in the Fall

  1. Mike Zachary

    I absolutely love this story and coverage of Stowe vs Woodstock. They’re both on my list to visit, and I’m using this story as my “things to do” guide. Thank You!

  2. Brian

    I thoroughly enjoyed reading the article on the comparison between Stowe and Woodstock in Vermont during the fall season. The vivid descriptions of the natural beauty, the charming small-town atmospheres, and the diverse activities in both towns make it a tough choice. Personally, I think the decision between Stowe and Woodstock ultimately comes down to individual preferences, but this article provides valuable insights for anyone planning a fall getaway in Vermont. Kudos to the author for capturing the essence of these two stunning destinations!

  3. Hunny K

    Such a helpful guide to deciding between Stowe and Woodstock for a fall retreat in Vermont! The detailed comparison really makes it easier to plan, and the descriptions of each town’s autumn charm are spot-on. Ready to embrace the fall foliage in one of these picturesque Vermont towns!


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