What Time of Year: July
Venue Location and Where I Stayed: The Williams Inn at Williams College
(Minimum 2 night stay at roughly $420/night so it's not cheap here)
Wedding Design: Barn Rustic, Greens, Suns and Moons (design by Unique Melody Events, day of set up by yours truly with the help of some fabulous assistants and the team of the Williams Inn and Flower Blossom Design)
If you are coming out here for a wedding or planning to have your wedding here, there are other hotels in the town to stay for cheaper but this Inn was built in 2019 so it was a luxury stay for sure. It also had a restaurant in the Inn which had some incredible food.
On my drive out from Central MA, I stopped in Shelburne Falls to see the Bridge of Flowers. I felt like I was transported back to Giverny in Monet's gardens. It also broke up the 2.5 hour drive from the Worcester area. Williamstown was under an hour from Shelburne Falls. If you don't want to drive to Williamstown, there is a small airport nearby in North Adams that people from NY seemed to be using.
Williamstown is home to Williams College which is a small liberal arts school that takes pride in their theater and arts programs. In July and August, they have the Williamstown Theater Festival.
Other things to do and see in town:
Hopkins Observatory (oldest extant observatory in the US)
Places to Eat in Town:
Thai/Japanese: Blue Mango
Good All Around Food: The Barn at the Williams Inn
Ice Cream: Lickety Split (everyone recommended trying the New England Choc Chip which was homemade maple ice cream with chocolate chips)
Things to do in surrounding towns:
MA Museum of Contemporary Art in North Adams
Tanglewood in Lenox
Berkshire Theatre Group in Pittsfield
Norman Rockwell Museum in Stockbridge
Kripalu for yoga and health retreats in Stockbridge