Katie and Spencer

Wedding Proposal Ideas in Portland, Maine

How We Met

Spencer and I met in November of 2015, when we were both seniors at the University of Connecticut. We spent the first chapter of our relationship celebrating the last few months of college, supporting each other as we looked for post-grad jobs. Although it was unspoken, it was assumed that we would try to get jobs in the same area, adding additional pressure on the job search. Thankfully, we both got job offers and started working weeks before graduation, diving right into the working world.

After a year living at home and starting our careers, Spencer and I took a big step and moved to Boston together. I got a new job and with two weeks notice, Spencer had agreed to pack up his life and take on a new adventure with me. Spencer caught my travel bug, and so far we’ve had to opportunity to visit Portland, Maine; Austin, Texas; Nashville, Tennessee; Atlanta, Georgia; Rome, Italy; Florence, Italy; Cinque Terre, Italy; Brussels, Belgium; Amsterdam, Netherlands; and Natal, Brazil.

Almost exactly four years since we’ve met, Spencer and I are two UConn Huskies, living in Boston, eating lots of lobster rolls and frequenting karaoke bars.

Marriage Proposal Ideas in Portland, Maine

Where to Propose in Portland, Maine

Engagement Proposal Ideas in Portland, Maine

How They Asked

Weeks before our engagement, Spencer told me to block off November 2nd on my calendar, as he was going to plan a surprise adventure. On November 2nd, 2019, we woke up, bundled up and got in the car. Spencer was really excited about the day and revealed that our trip was going up to Portland, Maine, one of our absolute favorite places.

When we got to Portland, we went straight to Allagash Brewing Company where we were greeted by three of our closest friends. After a brewery tour and a few beers, we got lunch at a local bbq restaurant and headed to Old Port, Portland. We were walking around for a while when Spencer and our friend Jared disappeared. They came back a few minutes later, announcing that Spencer had booked a private boat tour of Casco Bay. I was beyond excited, I love boating and thought it was such a thoughtful thing to plan.

We grabbed wine and Prosecco at a local package store, and got on board. It was a beautiful fall day, and it was so picturesque being out on the water with everyone that I thought to myself, “this would be the perfect place for him to propose.”

About 45 minutes later, we pulled up next to a light house. Spencer offered to take pictures of our friends and then we switched places so that they could take pictures of us at the back of the boat. Spencer asked me to turn around and check out the scenery, and when I turned back around, the first thing I saw was our friend Lauren crying. When I looked down, Spencer was on one knee! The rest of the day was so surreal, making calls and texting friends. It was absolutely magical, and I can’t wait to go relive that day each year on what is now going to be our annual Portland weekend.