Hues of reds, oranges, and golds painted the backdrop for Allison and Brandon’s wedding at Tanglewood. A fall chill was in the air, but warm apple cider was served to guests – a comforting and inviting touch to the day. The lawn in front of Highwood filled up with all of Brandon and Allison’s favorite people right as the sun began to set.

Stonover Farm in Lenox, Massachusetts, is a Berkshire wedding venue that exudes rustic charm and elegance. The property’s signature feature: distinctive blue trim on all the buildings around the property, making for instantly recognizable and Instagram-worthy photos.

At the end of the evening, I stole Mary, Ty, Megan and Brandon away for a little adventure. I loaded the foursome into my car and drove them down the road to High Lawn Farm for some couple portraits in the golden hues of a Berkshire sunset.

Suzanne, a local farm owner, had a passion for knitting, wool, and moving to the Berkshires. So together with her husband, they revitalized the old pastures, repaired existing buildings and completely brought this old dairy farm back to life.

A wedding at Wheatleigh Hotel in the Berkshires epitomizes elegance and charm. Nestled in the picturesque landscape of Lenox, Massachusetts, this small 19-room hotel boasts an Italianate-style that transports you to a villa right out of Italy.

Allie spent many summers on the Cape with her family and Skaket Beach holds a special place in their hearts. That’s why The Wequassett Resort & Golf Club provided the perfect setting for their special day, with its breathtaking views of Pleasant Bay. Ten years after that first date, their favorite people would make the trip to Cape Cod to witness Allie and Connor finally making their commitment official.

Do you have a crush on me, Matt Mitchell?”

Sometimes, all it takes is one courageous question to change the course of your life. For Sarah, it was a straightforward query to Matt Mitchell that set the wheels in motion for their love story. And YES, yes he did have a crush on Sarah. Love often leads us on unexpected journeys, for Matt, it meant moving across the state putting down roots in Sarah’s hometown here in the Berkshires.

Underneath a shimmering disco ball, friends and family gathered to celebrate the couple’s journey into marriage. Hailing from Washington, D.C., the couple shared a special connection with the band With Ford Bronco, a 90s cover band. Having the band perform at their wedding was a dream come true.

For Grace and Lachlan, their love story was woven right into the fabric of their childhood neighborhood. Living just houses apart, they navigated their adolescent years on Cliffwood Street before a chance meeting initiated by Grace’s father happened over “burger night” at nearby Firefly Pub.