Woodstock Inn and Resort Wedding Weekend

Kristen and Jim’s Vermont wedding weekend at the Woodstock Inn & Resort was absolutely incredible! The entire weekend had the vibe of a corporate team-building event meets wedding. Their wedding weekend blended team building, family, and their love perfectly, making it uniquely them! Kristen and Jim currently reside in Colorado, but they wanted to showcase everything the area has to offer. Guest experience was their top priority throughout the entire weekend.

Jim’s parents purchased a small vacation condo at the top of Quechee Mountain in 1980. They eventually decided to move to Quechee full-time in 1993, building their dream house to share with their kids and grandkids. Their plan was wildly successful, and Quechee has become a special place for their four children, their spouses, and 11 grandchildren! Kristen and Jim crafted the perfect laid-back yet extravagant wedding weekend affair.

Wedding Planner for New England Destination Wedding

For over a year we planned the ideal weekend itinerary filled with personal details and plenty of time for family. We organized guests into five groups: his friends, his family, her friends, her family, and their colleagues. The goal was to make everyone “Team K&J” by the time the ceremony took place. One of the overarching themes was “trees,” which we incorporated creatively throughout the design. Kirsten’s love of trees, she often sends Jim photos of unique trees from her travels and now jim sends her photos of trees from HIS travels. We leaned into the trees because of that and then the idea of the family tree flowed from there.

The weekend kicked off Thursday night with a casual pasta party. We joked that it was carb-loading before a marathon, which everyone loved! Guests received personalized welcome bags filled with Vermont specialties, including maple sugar candy, in handmade bags. They also received a family tree chart to show how everyone was connected, along with color-coded lanyards matching the family tree. These lanyards determined which team they were on for the welcome party the next day. Ben Schaefer from Silver + Salt was on-site all weekend, capturing every moment in a candid, documentary style.

Wedding Welcome Party in Quechee, VT

On Friday morning, guests had their choice of five Vermont-themed activities: a fly fishing excursion, a golf tournament at the Woodstock Inn & Resort, a private tour of Billings Farm, lunch and a glass-blowing tour and lunch at the legendary Simon Pearce, or a flower arranging class with Gregory Costa from Flou(e)r.

That evening, the welcome party took place at Murphy Farm at the Quechee Club. The night featured live music from Pat Dowling and games from GameOn VT, where guests competed for gift certificates to local businesses. Macs Maple set up a cart serving maple creemees. However, the highlight of the night was when the bride and her daughters danced and sang to Taylor Swift and Noah Kahan. “Stick Season” was even played twice—it was that well-received!

Wedding at The Woodstock Inn & Resort

The wedding day began with a planned hike up Mt. Peg. Initially, 98 out of 120 guests signed up for the hike. During the welcome party, I overheard guests asking if it was mandatory to hike. Later, the groom called to ask me about the likely attrition rate. I guessed about 25 would show up, and that’s roughly how many braved the weather!

Wedding morning hike in Woodstock, Vermont

The entire wedding morning was rainy, hot, and sticky, but spirits were high. That morning, I made the decision to move the ceremony indoors. The couple was thrilled not to have to make the call themselves and were able to stay present in the moment. We moved the ceremony to the Rockefeller Room at the Woodstock Inn & Resort, which we filled with lush greenery and white florals.

Getting ready for Woodstock Inn and Resort Wedding

Ceremony at the Woodstock Inn and Resort Wedding

New England Luxury Wedding Planner

The rain stopped just after the ceremony, allowing everyone to enjoy dinner and dancing in the stunning tent. Every detail was designed with the tree theme in mind. The entrance to the tent was lined with trees and greenery, and a central tree served as the escort card table. We chose clear rounded-back chairs and a rounded bar to echo the Vermont mountains. Guests enjoyed dinner and dancing by candlelight for an unforgettable evening.

The weekend concluded with a post-wedding brunch at the Woodstock Inn. Every aspect of this weekend was intentional and stunning and I was honored to bring their vision to life. We are so thrilled to have celebrated with Kristen and Jim!