Caitlin & James
Things To Do
Explore Portland
The Old Port has great bars, restaurants and shopping. We'd recommend stopping at Gritty McDuff's for a beer (bonus points, it's a Tottenham bar) and otherwise enjoying an amazing meal at Twelve (or any of the other restaurants by the water). Don't forget to stop at Beal's for the best ice cream in Maine!
Higgins Beach
Check out Higgins Beach (the best beach in the world) or any of the other amazing beaches on Maine's coastline. If you're at Higgins, getting a drink at the Higgins Beach Inn is an absolute must.
Enjoy a Lobster Roll
Check out the Lobster Shack at Two Lights in Cape Elizabeth for James' proclaimed "best lobster rolls in Maine" (or if you're Caitlin, for "a great hotdog") with ocean views; although we don't think you can go wrong with any lobster roll in Maine.
Check out Maine's Brewery Scene
Our favorite is the Allegash Brewery right outside of Portland; although Portland is home to a number of breweries including Shipyard.
Old Orchard Pier
Classic New England pier with carnival rides. Must try the pier fries.
Watch a Sea Dogs Game
The Sea Dogs, the minor league baseball team for the Boston Red Sox, play at Hadlock Field in Portland. Schedule for 2025 season yet to be released.
Kettle Cove Ice Cream and Shack
"Best ice cream in the world" - Caitlin Haefner, 2019