The Top 10 Prettiest Small Towns In Vermont

Many people say that Vermont is one of the most beautiful places in all of New England. It is a place full of natural wonders, and there are communities here that are over 300 years old. So, it is hard to disagree.

The Top 10 Prettiest Small Towns In Vermont

Vermont is no huge metropolis. On the contrary, it is a place that offers the idyllic small-town getaway, and its top ten prettiest towns are a testament to that.

So, if you’re interested in getting out of the city and experiencing a slower way of living, be sure to check out these top 10 prettiest small towns in all of Vermont. If you’re interested, read on for more!

Here are our top picks for the 10 prettiest small towns in Vermont. Do you agree?

1. Manchester

Manchester is a Green Mountain town located in Vermont, and it has a wonderful balance between modern comforts and that quaint, antique, small-town charm.

You can spend the day exploring all of the rustic beauty Manchester, Vermont has to offer and then get dressed up for a fine dining experience for dinner.

There are many places where you can relax in luxurious settings, or you can choose to walk around and learn everything you can about the history of New England.

Whatever you choose to do in Manchester, you are sure to have fun and feel rejuvenated.

2. Weston

Weston is a quirky little town full of vintage charm.

There’s plenty to see and do here, such as learning about history at the Vermont Scale Museum, or exploring unique, antique attractions such as the largest collection of weather vanes in the entirety of New England!

Weston is also home to a fantastic theatre and art galleries, and there are plenty of restaurants to eat and people-watch.

Of course, the best time to visit this pretty Vermont town is during the Christmas season! Weston is best known for its Christmas stores and you can spend hours exploring all of them and finding the perfect gifts for your family and friends.

3. Lincoln

If you wander deep enough into the Green Mountains, you will find a little, pretty town called Lincoln, nestled into the greenery. Lincoln was once home to a large community of Quakers.

And, even though they no longer live there, their influence is still significant. Tourists can visit Quaker street and see where this society gathered and how they lived. If you’re interested in history, there is plenty of it to be found at Lincoln.

These days, Lincoln is famous for being a ski retreat. It is not too far from the Sugarbush Ski and Mad River Glen areas, so it is the ideal base camp for a winter vacation. Stay at Lincoln and wake up to rolling mountains and a lush landscape every day!

4. Stowe

If you were to travel through the valley between the Green Mountains and Worcester Range, you would eventually stumble across Stowe, a wonderful settlement where early settlers chose to build their lives!

As you can imagine, Stowe is a beautiful small town full of a close-knit community feel. You will be made to feel like family here, and you can experience a cozier way of living by exploring the many community festivals and craft fairs that Stowe has to offer.

Stowe hosts a British Invasion during the early fall, and you will be able to check out some awesome British car models. Alternatively, you can visit in the summer when you can choose to see a variety of theater shows.

And of course, Stowe becomes home to many tourists with a passion for skiing in the winter.

So, if you enjoy close family life, theater shows, cars, skiing, or a simple hiking nature trail, be sure to check out the wonderful little Stowe.

5. Grafton

Grafton is one of the most historic villages in all of New England. It can be found in the southern parts of the Green Mountain, and it retains plenty of the mountain culture of the past.

Visitors will immediately notice how well-kept their town center is, and how well the history of Grafton and New England is preserved in the many history museums.

Not only that, but Grafton is a pretty town where tourists can enjoy the outdoors! It boasts the wonderful Grafton Ponds Outdoor Center, where visitors can spend the day enjoying the best nature Vermont has to offer.

Or, during bad weather, you can explore both the Plummer’s Sugar House and the Grafton Cheese Village!

6. Shelburne

Shelburne is but a stone’s throw away from Burlington, the biggest city in all of Vermont. However, it could not be more different! Shelburne has that classic small-town feel, and visitors will be able to enjoy many quaint activities throughout this beautiful place.

For example, you can brush up on your history knowledge at the Shelburne museum or the Covered Bridge museum, or you can spend the day relaxing with a loved one at Lake Champlain.

There are also many beautiful parks where you can relax and clear your head, surrounded by tranquil nature.

7. Montpelier

Montpelier is not -technically- a small town, being the Capital city of Vermont and all. However, it has the distinct feel of a small town. Having only 8,000 residents, it is the least-populated city in the whole of the US with many characteristic red-brick buildings.

So, the streets often feel quiet depending on how many commuters are out and about. Montpelier is more like Manchester or Shelburne than it is New York or Chicago. For these reasons, it has made the list!

Visitors to Montpelier can check out the wonderful Vermont History Museum or Vermont State House, as well as the peaceful Hubbard Park, where the fall hues, many picnic areas, sledding hill, soccer field, and white stone observation tower make it feel like something out of a children’s fairytale.

8. Dorset

Engulfed by rolling hills and nestled into the valley, Dorset is representative of quintessential small-town life.

It can sometimes feel like a lively city with parades rushing through the streets and festivals with pleasant music that permeates the walls, but Dorset is also the place to go when you want to get away from it all and have a quiet getaway.

Tourists can find peace in nature at Emerald Lake State Park, where they can unwind by the lake or walk amongst the greenery.

If you’re the more introverted type and love taking a good book to the park and losing yourself in the pages – then Dorset is the place to do just that!

9. Woodstock

Woodstock is a town that has existed since before the creation of the United States. This old town still has streets from its pre-revolutionary era, and visitors can walk through them and learn about this important part of history.

Not only that, but the architecture built here spans many eras of history, and visiting Woodstock is like walking through time.

If visiting, be sure to check out the vast array of bridges as well as the many museums and historic sites. If there’s one place you’ll learn about history, it’s Woodstock!

10. Chester

If you’re looking for an outdoor getaway to remember, then you need to visit the beautiful Chester! This pretty little Vermont town is situated near three state forests, where tourists have the opportunity to explore, hike, or simply watch the wildlife.

This is the perfect place for those who love adventure and making memories. And, if you want a different experience of nature, the Stoughton Pond Recreation Area is a gorgeous place to spend the day.

However, Chester is also home to many historic streets and shopping areas, so you can enjoy some retail therapy with a view here, too!

Final Thoughts

Vermont, New England, is home to some of the prettiest towns you will ever visit! In all of these towns, you have the opportunity to bask in nature, learn about history, or enjoy plenty of entertainment!

Alex Kallen
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