Pleasant Bay Soiree ⋆ Winslow Estate ⋆ Orleans, MA


On June 21, 2019 there was a big “Claws for Celebration” here on Cape Cod.

With Eliza + George set to get married the following afternoon, at Eliza’s lovely family estate in Chatham, we planned an equally elevated celebration on Pleasant Bay for the night before.


When I first chatted with George, their original wedding rehearsal location wasn’t playing out the way that they had hoped. He asked me to help with venue sourcing for them so I spent the next week reaching out to all my favorite venues, restaurants and estates within a 20 minute radius of Saturday’s Chatham wedding location. I knew I’d hit many dead ends, with it being such a popular date here on Cape Cod, but I also knew that my local knowledge would help to find the perfect fit. When I went to check in on the Winslow Estate’s availability, I was shocked to see that the exact dates needed were the only ones left for June. The expansive views of Pleasant Bay were an easy sell and we happily pushed forward transforming the front lawn of Gentle Heritage into a tented rehearsal dinner.

This family was so lovely to work with from start to finish as they aimed to ensure their guest experience was exceptional. George had only a few must haves that he set from the start: an interactive airstream bar, a laid-back clambake style meal, and passed trays of Bud Light bottles - check, check and check. With the top 3 needs addressed - George handed off much of the remaining planning to his sister, Allyson, who nailed design decisions and weighed in with thoughtful event concepts, plus utilized her trained eye. Each and every choice had a special level thought given towards her brother and his soon-to-be wife. Her input led to many of the show-stopping and most commented upon on moments of the night from the adorable escort card pails, interactive flower crown station and thoughtful stationery elements.


To capture Eliza’s free-spirited style the request was for wild, unkept flowers teeming out of vessels as they stretched outwards across the center of the Nantucket Driftwood farm tables. For that natural, imperfect feel I knew that sustainable florist, Millie Rochon of Whitemoss and Twigs, would deliver on arrangements that stray from “traditional” Cape Cod. The florals were delicately lit from above by a mix of bistro lights and paper lanterns hanging from the sailcloth tent ceiling - all perfected by the team at Undercover Tent. With the family’s roots on Nantucket the particular wash of the tables from True North felt like the perfect match.


The forecast teetered and tottered throughout the week with signs of a clear up in store for Friday night. However, at the final hour, it appeared there’d still be rain on the forecast and luckily we had a plan for Hive’s Airstream Bar to fit beneath the cocktail hour’s tent so that the guests would remain dry while placing their drink orders. That afternoon, the Hive team arrived early so that we could finesse their Airstream into position. Finesse, truthfully, may not be the right word for it but a few sheets of plywood and 25-point turns later we were in business! Having the additional cozy seating area within the airstream created a desirable space for guests to hang, relax and enjoy which was so valuable on the drizzly night.


From appetizers through to the “main event” the Clambakes, Etc. team served delicious bites and massive plates of seafood. The appetizers were innovative and fresh while the meal was a classic, bountiful pot style clambake … the perfect balance. Guest’s eyes grew huge with excitement as they looked at their overflowing dinner plates and quickly got to business twisting and cracking open their lobsters. There was no question on “How to Eat a Lobster”, with easy-to-folllow, custom cards plus everyone stayed stain free with custom wet wipes and lobster bibs included in each guest’s personalized pail.


Really, how sweet it all was! The team at Ellie’s Providence served table-side ice cream sandwiches, with their ice cream cart, as a finishing touch for the meals. Guests had the difficult choice of: mint chocolate chip on a mini macaron, cookies and cream on a homemade chocolate shortbread and last but not least coffee ice cream on a toffee chip cookie. If you guessed that some guest’s weren’t up for the tough choice and in fact tried all three (or more), instead - you’d be correct.

Finally, with the help of Cape Destinations, guests were sent off to welcome drinks at the ever-popular Bistro on Main.

Cheers to all who helped plan this special evening and cheers to Eliza and George who were now, one day closer to husband and wife!!

Vendor List:

Photography: Keslie Corbett Photography

Tent Rental and Lighting: Undercover Tent

Tables and Chairs: True North Event Rentals

Florist + Flower Crown Station: Whitemoss and Twigs

Catering: Clambakes, Etc.

Planning and Design: Daylynn Designs

Airstream Bar: Hive Events

Mini Ice Cream Sandwiches: Ellie’s Providence

Stationery: Modern Vintage

Venue: Winslow Estate

Tabletop Rentals: Peak Event Services

Transportation: Cape Destinations

Rachel LynnComment