Looking for the perfect fall getaway? Look no further than Woodstock, Vermont. Oozing with Norman Rockwell small-town charm, this New England town is picturesque and full of fun things to do.

Friday

We kicked off our long weekend Vermont road trip by flying into Boston and picking up our rental car. The drive from Boston to Woodstock is about 2.5 hours. The foliage on the drive up was breathtaking – you know when the highway is beautiful that you’re arriving just in time for peak foliage season. While the best time for fall colors varies each year, we arrived on October 15th and couldn’t have been happier with the foliage.

During our drive we stoped in Quechee to check out the gorge and at Sugarbush Farm in Woodstock to try some local cheese and maple syrup.

The Woodstock Inn was our home for 3 nights and could not have been more charming. The service was excellent and the staff attentive and kind.

Our evening concluded with dinner at Simon Pearce in Quechee. The restaurant overlooks Quechee Gorge and is located within a glassblowing studio/store that will make you feel like you walked on the set of Sweet Home Alabama.

Saturday

We got up early Saturday morning and made the 1.5 hour drive up to Stowe. We crammed so much into this day and are already planning to spend a few nights in Stowe next year! Here’s our activities hit list:

• Smugglers Notch Pass – A must for fall foliage! Go for a quick drive through the leaves or spend an entire day. There are many hiking paths along the road to get out and get some exercise.

• Lunch and local brews at the Von Trapp Family Lodge & Beerhall – Yes, those Von Trapps. After fleeing Austria, the family settled here in Stowe. Make a reservation online in advance! This spot fills up quickly and the walk-in line is long.
• Cold Hollow Cider Mill – For everything apple cider – apple cider donuts, hot apple cider, apple cider slushees, and the hard cider variation. Fun for the whole family.
• Stowe Cider – Hard cider in every flavor under the sun.
• Cable car up Mount Mansfield
• Biking along Stowe Recreation Path
• Hike up Stowe Pinnacle
• Gold Brook Bridge (aka Emily’s Bridge) – 1 of the many covered bridges in Vermont.
• Ben & Jerry’s Factory
• Dinner at Edson Hill

Sunday

We had a leisurely Sunday morning with breakfast at the Inn and a stroll around town. Woodstock did not get crowded until lunch time, so we had the town to ourselves that morning.

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In the afternoon, we drove to Killington (apx. 20 min away) and had our first ice-cream of the day at Madd Hatter’s Scoops. We then checked out Sleepy Hollow Farm in Woodstock. I saw a picture of it on Instagram and had to check it out. Note that this is really just a residential neighborhood. It’s definitely worth the drive since the views on the way are incredibly scenic, but don’t expect a working farm where you can tour/visit the operations.

Our second ice-cream of the day came from Mountain Creamery, a local spot. Work off the ice-cream on one of the may trails in Mount Tom or Mount Peg.

Dinner was at Worthy Kitchen – the best burger in town!

Monday

After another leisurely morning at the Inn, we stopped by Billings Farm to meet some friendly farm animals and have more ice-cream. The farm is in walking distance of the Inn and include a museaum with art and other local exhibits.

Sadly, all good things must come to an end. On Monday, we made our way back to Boston for our flight home and stopped in Cambridge for lunch at Russell House Tavern on the way. We can’t wait to head back to Vermont next fall!