As the third largest town in Vermont, Bennington has quite the cultural flair. There is so much going on in this town, lovingly called the shires, that it’s next to impossible to see and do everything- unless you’re staying for at least a week. Aside from the picturesque views, incredibly friendly locals, and trendy breweries, this town has something for everybody. And with ties to Norman Rockwell, Robert Frost, Ethan Allen, and General Stark – how can you not want to go visit this sweet All-American town.

To help you plan a trip, here is a list of the top 15 things to do in Bennington VT

1. Vermont Begins Here – right before your trip, make sure that you check VermontBeginsHere.com because it’ll have a rundown on all of the events going on for the weekend, so you definitely want to plan around anything that this town has going on. Because, quite simply, it’s a fun time.

2. Stay at the Four Chimneys Inn – This is the epitome of Vermont, located in a cozy little mountain town with an elegant, traditional style. The original building dates back to 1783 and belonged to a Reverend. However, in 1910 the house burned to the ground, and the entire place had to be rebuilt. Before it became an iconic Inn it served as a fine dining establishment in the 1950s with notable clients like Elizabeth Taylor, Richard Burton and Walt Disney. In more recent times, it has been converted into a The Four Chimney’s Inn – giving you all the modern day amenities while holding on to all the classic New England charm. Love it, it’s one of my favorite Vermont Inns!

3. The Old First Church – This was the first Protestant church in Vermont. The first Protestant church was gathered in 1762 and they met in the meeting house in 1763. The present church was built in 1805 and sits on top of the hill with a stately etheral appearance. With its impeccable graveyard you can stroll through the marble tombstones and even visit Robert Frost’s grave.

4. Blue Benn Diner – visit a locals favorite – the Blue Benn diner, which has been in town for 48 years. You can sit at the counter and get a good cup of coffee, or sit in a quaint 70’s style booth. The pancakes are the best pancakes I’ve ever had. And they even make homemade in house fresh doughnuts!

5. Go on a Covered Bridge Tour – There are three bridge covered bridges within 10 minutes of Bennington. and the old Norman Rockwell covered bridge is about 30 minutes North, and it’s a beautiful drive. Note: If you’re visiting during fall, and you get there early in the morning, you’ll be able to see the fog as it settles down around the mountains and surrounds the church and the bridge.

6. Hildene – Hildene is the Lincoln family residence. Not far from Bennington, you’re able to tour the grounds with immaculate gardens, and even take a look inside the stunning house. It was home to numerous generations of Abraham Lincoln’s family.

7. Powers market – This market was originally a country store and built in 1840 making it oldest country store in Vermont. You can grab a cup of coffee, and some delicious pastries, or even grab lunch at the deli.

8. The Bennington Battle Monument – This monument stands at 306 feet high as a stone obelisk. It commemorates the Battle of Bennington from the American Revolutionary War. If you climb to the observatory level at 200 feet you can see along Vermont, and even the US states of Massachusetts and New York.

9. Visit the Village Chocolate Shop – Take a peek inside the ever adorable Village Chocolate Shop. Make sure to try the dark chocolate sea salt covered caramels. And some of their ice cream.

10.  Bennington Museum –  I loved strolling through this old museum, with the bold collections of art and regional history. It’s a great way to spend your afternoon. The museum also has the largest collection of Grandma Moses paintings, which are displayed in the school house. While walking around exploring the paintings, you can even watch a video of an old interview with Grandma Moses, and it was fascinating.

11. Bennington Potters – no stop in Bennington would be complete without a stop to  Bennington Potters. This is the largest working craft pottery in the United States. You’re allowed to tour the manufacturing area and learn process from the potters themselves. It’s also a great place to pick up presents for loved ones.

12 Visit the doll house and Toy Museum of Vermont –  This museum is open Saturday and Sunday from 1 to 4pm year round, and holiday afternoons. You can see a collection of doll houses that sample from Cape Cod houses to elaborate Victorian houses. There’s also trains and trucks to appeal to everyone.

13. Madison Brewing Company – While exploring downtown Bennington, stop into Madison Brewing Company to grab a bite to eat and try their craft beer, that’s brewed in-house. If you’re visiting during the autumn, you definitely have to try their pumpkin harvest Ale, which is brilliant. It has only a hint of pumpkin. And they rim, the glass with cinnamon and sugar, and it tastes divine. A popular hangout for the locals this place is sure to satisfy everyone.

14. The Four Corners –  Be sure to check out the spot known as the four corners, which most consider the center of Bennington. In the center of the intersection is a North Star Compass surrounded by piano keys painted into the pavement.  Polly van der Linde planned the design, wanting to create happiness with a focus on the  thriving art scene in Bennington.   Between the  bustling little intersection, a historic town clock, and the street art, its easy to see Bennington’s community spirit!

15. The Apple Barn and Country Bake Shop – Take time to stop in the Apple Barn and explore the Vermont grown fruits and vegetables. You’ll also find local honey, fresh baked baked breads, regional cheeses, and my favorite, the cider donuts.

What are your favorite things to do in Bennington VT?

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