1-Day Itinerary in Southwest Vermont

Last Updated on April 13, 2024 by Adam Watts

We recently took a drive north out of New York and, guys, let me tell you, it’s like another world up there! We were gone two nights and here’s my recommendation for a condensed 1-day itinerary in southwest Vermont. The Green Mountain State is beautiful though, so if you just feel like driving around or hiking someplace, have at it. Don’t let me force you into doing any of the activities below.

For breakfast, head to either Bennington or Manchester for a slice of quiet country life and a strong cup of joe. If you go to Manchester, I recommend The Works Café. This is your first reminder that life up here isn’t fast-paced. If you had to wait for your coffee because the barista was chinwagging with a local about the health of their neighbor’s daughter’s cat, resist the urge to get involved with a snarky comment like you would in New York.

Once you’re fed and watered – even if it takes you an hour and a half – depending on where you are, check out the Bennington Monument ($5 to get views of three states from the top on a clear day) or the Manchester Riverwalk (free). If you’re in Manchester, also check out the Northshire Bookstore, but be warned, you might lose half your day inside.

When you’re ready – and let me stress this again: don’t rush! – jump back in your car and head north on Route 7A to the Lincoln Family Home at Hildene ($23 adults, $6 for 6-16 year olds, and under 6s go free), one of the star attraction of southwest Vermont.

The house itself, I’ll be honest here, isn’t that exciting, unless you’re a huge fan of Georgian architecture or for some reason you’re particularly fascinated by the comings and goings of presidents’ children. (Robert Lincoln was the only child of Abraham and Mary Todd Lincoln to survive to maturity.)

What’s more appealing is everything around the grounds that isn’t the house. Behind the house is a formal garden with great views over the surrounding countryside. There’s the Sunbeam Pullman Car, a train carriage from 1903, with some interesting history: when Robert Lincoln was president of the company, Pullman became the largest manufacturing company in the world. There are also a few trails to stroll, amble, mosey, sashay, or wander, depending on your preferred style of easy-living. (We went for a nice amble.)

Lastly, there’s the goat dairy farm. We stumbled upon it a little before 3pm, when the milking process starts. The goats crowded around, waiting to be let into the milking chamber. Two of them were locked in some kind of territorial dispute and kept standing up on two legs and launching themselves onto the other one. It was very odd, but foreplay is foreplay I suppose, who am I to judge?

We stood outside the glass as voyeurs watching the goats be removed unceremoniously of their milk, but I shan’t go into exact details since this is a family-friendly post. Suffice to say I had some funny feelings while watching.

Depending on how long you spend at Hildene, your final stop of the day should be at Lake Shaftesbury State Park, just one of many similar places in southwest Vermont. It’s a picture-perfect lake with a small patch of beach and enough picnic tables to seat an army. Perfect for kids, but just as pleasant for adults too: hopefully you remembered to pack a frisbee, a good book, bathing suit, and towel.

Once the sun goes down, or when your stomach starts calling, head back to Manchester and get a table at Ye Olde Tavern, dating from 1790 when Vermont was still an independent republic. The place is super cosy and the food is delicious – don’t miss the complimentary cranberry fritters with Vermont maple butter. Sunday through Friday they offer an early bird special (5-6pm) for those looking to save a dime or two.

Vermont is more laid back than a first-class berth on an Emirates flight, and much cheaper. If you’re coming from NYC or Boston or for some remarkable reason you’re coming all the way to southwest Vermont from San Francisco or LA, this corner of the world is a perfect getaway from big-city living. No one’s in a rush here, no one’s hurling abuse at one another in the street, and besides a few freaky goats, no one is trying to get one over on anyone else. It’s just peaceful, and chill, and relaxed, and you’ll have a god-dang nice time. What more can you ask for?