New England Lakeside Wedding

November 12, 2025

A Lake Winnipesaukee Wedding to Remember: Ali & Jack’s Elegant Celebration at Brewster Academy

If you’ve ever dreamed of a New Hampshire lakeside wedding, Ali and Jack’s stunning celebration at Brewster Academy in Wolfeboro is sure to inspire. Planned and designed by Events by Sorrell, the weekend was the perfect blend of heartfelt moments, coastal elegance, and timeless New England charm. With views of Lake Winnipesaukee, thoughtful personal touches, and an unforgettable party under a sailcloth tent, it was a true highlight of the summer season.

The Perfect Start: A Weekend at The Pickering House Inn

The couple and many of their guests stayed at the Pickering House Inn, a beautifully restored property in downtown Wolfeboro. On Thursday evening, they hosted their rehearsal dinner there — a warm and welcoming gathering that set the tone for the weekend ahead. The bride and groom also got ready at The Pickering House, surrounded by close family and friends, making it an especially meaningful start to their celebration.

A Lakeside Welcome Party Filled with Coastal Charm

Friday’s welcome party, designed by Events by Sorrell and catered by The White Apron, perfectly captured the relaxed beauty of the Lakes Region. With tables set beside the water and cheerful umbrellas shading guests, the scene felt effortlessly coastal and inviting. The atmosphere was full of laughter, summer breezes, and the sound of clinking glasses as guests toasted to the weekend ahead — a joyful prelude to the festivities to come.

A Heartfelt Ceremony in the Heart of Wolfeboro

The wedding ceremony took place at the Wolfeboro Congregational Church, just steps from Brewster Academy. Surrounded by nearly 300 guests, Ali and Jack exchanged heartfelt vows accompanied by elegant live music from Music Management out of Boston. Following the ceremony, a bagpiper led guests down to the lakeside reception — a charming and truly memorable New England touch.

Before joining their guests, Ali and Jack took a quiet moment together, enjoying a romantic ride across Lake Winnipesaukee in a vintage Chris-Craft boat. Watching them glide across the water, just the two of them, was one of my favorite moments of the day — peaceful, joyful, and a perfect way to savor their first moments as newlyweds.

A Sailcloth Tent Reception Beside Lake Winnipesaukee

The Brewster Academy wedding reception, beautifully coordinated by Events by Sorrell, was held under a sweeping sailcloth tent right on the water’s edge. The design was understated yet elegant — soft white linens, natural greenery, white chairs with subtle blue accents, and a full wooden dance floor that stayed lively all night long.

Guests were welcomed by a custom golf-themed seating chart created by the couple themselves, featuring golf tees with each guest’s name — a playful nod to their shared love of the game. The White Apron once again delivered exceptional food and bar service, while The Sultans filled the tent with incredible live music that kept guests dancing well into the night.

As the sun set over Lake Winnipesaukee, the glow of the sailcloth tent reflected on the water — a picture-perfect ending to an unforgettable day filled with laughter, love, and coastal sophistication.

A Timeless New England Wedding Experience

Planned by Events by Sorrell, Ali and Jack’s Brewster Academy wedding was everything a New Hampshire summer wedding should be — elegant yet relaxed, beautifully personal, and surrounded by natural beauty. From the Pickering House rehearsal dinner to the coastal-inspired welcome party and the romantic boat ride across Lake Winnipesaukee, every detail reflected the couple’s love story and the timeless charm of a lakeside New England celebration.