The night my fiancée and I got engaged I said, “Let’s not talk about any wedding plans for at least two weeks, and just enjoy some time being engaged.” The next morning as we were lying in bed, we all but played a game of “20 Questions” about what we wanted our day to look like, both of us fielding ideas off of each other. Three weeks later, we had a date selected and a deposit down on our venue! So much for slowing down.

I don’t regret jumping into planning. It was so much fun to talk about what we both envisioned for the day, and really hard not to once there was the reality of it sparkling on my left hand. It feels really good to have, in my opinion, the two most critical aspects of our wedding day solidified—the date and the place. Now I feel like is the time when we are enjoying being engaged the most because we are not worrying about the “when” or  “where.”

We ultimately decided to move so quickly on those critical first planning steps because we knew that we really wanted to get married in Provincetown. Of all the things that our wedding could be—all of the shapes it could take, time of year it could be, and other details—being in Provincetown was the most important to both of us.

Here's how we decided to get married in Provincetown, Massachusetts sunset beach
Photo courtesy of Maggie Kilgallon

To make that happen, we knew that we would have to work within the constraints of Provincetown’s size and offerings. Part of what makes PTown so charming to us is that it is small and quaint. However, that means that there are only so many people we could invite and only so many places we could hold a reception like the one we have in mind. Since we are so familiar with PTown, we had a good understanding of what might be possible for the wedding we imagined. What we were less sure of were the capabilities and possible accommodations of each of the venues on our shortlist, and if there were any other venues out there that we did not know about.

We were both obsessed with a wedding that an event planner called “The Little Things” put together last summer. We’d stumbled upon photos of this particular wedding on Instagram and were absolutely charmed. Those photos and the complete event that was put together for that couple is ultimately what led us to want to get married in PTown versus closer to home. It showed that it was possible, that it would allow for so much creativity and personalization, and that it would be “us.”

We loved the wedding that The Little Things put together so much that we decided to have a consultative phone call with the event director, Alexis. We had such a great and informative conversation with her about what a wedding planner could offer us, but ultimately, it was way outside our budget. We also realized that ‘the little things’ this wedding planner specializes in are not what is most important to us. Surprised but not disappointed, we decided to pursue other options that made more sense for us and our vision.

We (okay, my fiancée, Kelli, not me) researched essentially every wedding venue option there is available in Provincetown, including outdoor spaces and public areas such as the Provincetown Town Hall. She submitted queries online and made phone calls. By process of elimination (too small, limited availability, too expensive, food would need to be catered) we narrowed our list down to two places: The Provincetown Inn and the Pilgrim House.

Here's how we decided to get married in Provincetown, Massachusetts
Photo via Pilgrim House

The Provincetown Inn would have been able to accommodate more people than the Pilgrim House, but some of the downsides for us, especially when compared to the Pilgrim House, were that it is kind of far off the beaten path (in other words, far from Commercial Street). We also had never stayed there before. The Pilgrim House was the first place we stayed together in Provincetown, back when it was still called the Sage Inn. It was one of the coldest weekends we have ever experienced in Provincetown—negative 10 degrees with the wind chill, and snowy—but one of the best. We got to know each other in deeper ways that weekend, as we celebrated Kelli’s birthday and explored Provincetown in the offseason. We had so much time with just the two of us, a rarity in PTown when you travel during peak season. We also had the opportunity to talk with people who live there all year long, immersing ourselves a bit more in the culture of the town. 

We go back to the Pilgrim House every time we go to PTown, even if just for a drink or to see a show. We know the space well, and we love it! We have always had wonderful drinks and food there, and have never had anything but pleasant interactions with all of the staff. When it came down to making a decision, the Pilgrim House was a no brainer for these reasons alone, but we considered a number of other, very practical things to help us make our decision, including cost, location, size, food and beverage options and availability. The Pilgrim House was able to give us a very robust and reasonably priced package for our whole wedding weekend, which was exactly what we were looking for and more.

After we booked our wedding date, we made a plan to travel down to Provincetown and meet with the event manager, David, to get a personalized tour of the grounds and run through more specific details about what we wanted the day to be.

Here's how we decided to get married in Provincetown, Massachusetts
Photo via Pilgrim House

Sitting down with our event manager was intimidating, thrilling and ultimately so fun and exciting. I wasn’t sure what to expect at first. We started off by going over the very basics: Confirming the wedding date and setting a schedule of events. We decided that we wanted to have our wedding on the beach (weather permitting) at sunset. David went so far as to research a year and a half in the future to what time the sun would be setting on our wedding day, in order to ensure that we would have optimal lighting for our ceremony and for our pictures (which we will be taking after the ceremony). He also had the forethought to look ahead to the tide cycle on that day to confirm that there would be a beach to have our wedding on. There’s not a lot of sense in having a beach wedding if the tide is high and there is nowhere for people to go!

We discussed the pros and cons of a plated or a buffet dinner for a group of our size, ultimately opting for the plated option. We made plans for a cocktail hour with passed hor d’oeuvres and a champagne toast for when we return to the inn after taking post-ceremony photos. We discussed dinner seating plans and dancing space. David was also able to provide us with the name of a local DJ he has worked with and who would be open to one of our unique requests for the evening, including a surprise performance by a drag queen. In addition to the DJ recommendation, David was able to provide recommendations for queens as well (and we are so excited about this part of the wedding).

Finally, since Kelli and I met at an ice cream shop, we talked with David about forgoing cake and opting for an ice cream bar instead. He didn’t flinch at the idea (which will inevitably cause more work for his team). He was all for it and talked us through how we could set up and serve it. We even picked our flavors!

The experience of sitting down with our event planner at our wedding venue to go over important details and a rough run-through was so much fun. It made everything seem so real. We appreciated the time and attention to detail that was given to us. We feel very taken care of by the Pilgrim House staff already and we still have over a year to go until we get married. We are so glad that we made the choice to have our wedding there and are looking forward to all of the planning that is still to come!

Maggie Kilgallon head shotMaggie Kilgallon is a writer and marketing professional. She lives in Boston, Massachusetts with her fiancée. Maggie is a graduate of Boston College, where she majored in English and minored in Women’s & Gender Studies. In her spare time, she enjoys volunteering with empowerHER, going to concerts, working on her yoga practice and beachcombing with her fiancée.