Ali and Connor’s engagement session at Chesterwood in the Berkshires was filled with laughter, romance, and a few fun surprises (including a Taco Bell stop on the way home!).

The couple’s love story began at UMass Amherst, where they were next-door neighbors in the dorms. “We started as friends, but when I realized how smart and fun Connor was, I couldn’t help but fall in love with him,” Ali shares.

Connor’s proposal was just as thoughtful as their love story. While living in California, the two spent months exploring the Pacific Coast Highway. On their final stretch of the trip, Connor found a beautiful ocean overlook to pop the question, the perfect ending to Ali’s dream adventure.

When choosing a location for their engagement photos, the Berkshires felt like the perfect choice. “We fell in love with the beauty of the Berkshires and how it feels like a completely different world from the rest of Massachusetts. None of our family has any ties here, so it feels like a place that belongs to just the two of us.” says Ali.

As for the wedding day? “I am truly excited to finally be married to my best friend,” Ali says. “Having all our friends and family there to dance and enjoy good food will be the cherry on top!”

Ali and Connor, I loved every moment of your Chesterwood session and I can’t wait to capture your wedding this September

♥ Lisa