It was with heavy hearts that we left the idyllic town of Bar Harbor, but there was much more for us to see in beautiful Maine. We hit the road for a leisurely drive to Portland, taking the longer, coastal route and making a couple of fun stops along the way.
First up, a visit to Cellardoor Winery in Lincolnville. This beautiful property features an immaculately renovated barn from the 1790s and a gorgeous sprawling lawn with serene mountain views, proof that there’s a benefit to leaving the Maine coastline for a bit.
My sweet family was so kind to put up with the complications of traveling with a dog throughout the trip. Since he couldn’t go inside the tasting room, we took shifts tasting wine and gathered on the back patio for glasses of wine and cheese afterward even though it was mighty warm outside. I know it must have gotten annoying quick, but they were troopers.
Cellardoor is a very sophisticated operation, and we loved the old barn and the excellent customer service. They source their grapes from around the U.S. so they offer a little bit of everything. I was shocked to find that tastings were free as well as your first glass of wine. The rest of the family also enjoyed a wine tasting paired with local cheeses, which received rave reviews.
We couldn’t stay away from the water for too long, though. Next up, lunch in beautiful Damariscotta. Maine is just insanely pretty.
We enjoyed a dog-friendly lunch on the shaded patio of Schooner Landing, overlooking the Damariscotta River.
The food was just okay, but the views and a lively band made up for that. It was a nice way to break up the drive and fill our bellies.
After all our detours, we made it into Portland around dark and checked into our cozy home for the next two nights, The Inn at St. John. It was a change of pace to go from Bar Harbor, where pretty much everything was within walking distance, to a proper city. I’ll admit that I didn’t have enough time to plan activities or meals any further out than Bar Harbor, so the rest of the trip was go-with-the-flow. But that’s just when things tend to get the most interesting. With no plan whatsoever, we took a cab downtown near the Old Port in search of food and fun.
After a rushed dinner (restaurants seem to close rather early in Portland), we hit up Lincoln’s Speakeasy, which is pretty much the epitome of hipster awesomeness. Everything at Lincoln’s costs five dollars (get it?), cash only. For such cheap drinks, they make them strong so be warned. We had a great time playing a mostly PG-13 version of “Never Have I Ever” and tipsily toasting to “the journey” which became our motto for the rest of the trip. It really is all about the journey, you know?
The next morning got off to a slow start, but we eventually made our way out into the world for a light and tasty lunch at Sebago Brew Pub before heading to one of Portland’s most iconic sites.
We didn’t have time to do much sightseeing, but after talking to a few locals we knew we couldn’t miss Portland Head Light and Fort Williams Park on Cape Elizabeth, just a short drive outside the city. If you’re looking for postcard views, this is your spot.
Portland Head Light is the oldest lighthouse in Maine, dating back to 1791, and the surrounding 90-acre park is full of walking paths, historical sites and never-ending beauty.
Of course, we had the dog with us. He really is powerless to pass up a good water view and begged us to take a family photo to commemorate the occasion.
It was a blazing hot day. I was under the impression that Maine didn’t get too hot in the summers, but I was sorely mistaken. After wandering around for a bit and marveling at the scenery, we hightailed it to some air conditioning.
Our main Maine event was a 4th of July fireworks cruise in the Casco Bay. I’m a big fan of boats on the 4th of July. In 2011, I took my parents on a cruise on the Potomac out of Alexandria and again took my brother on a dinner boat in DC in 2013. It was nice to get the whole gang together this time around.
We had a good time dancing like no one was watching and enjoying that intoxicating feeling of being out on the open water on a beautiful night. It’s just one of my absolute favorite things.
It was our last night with my family before they returned to Oklahoma and we continued our road trip, and I can’t think of a better way to have ended such a special trip.
We all fell deeply in love with Maine, and I have a feeling we may just be back before too long.
It’s a shame that you didn’t post any photos of Lincoln’s Speakeasy as that would have been cool to see. But, I can’t believe you played “Never Have I’ve Ever” with your family. That game can get pretty racy pretty quickly, especially after a few too many drinks. 😉
It was too dark inside to get any pictures with my limited skills, but I’m bummed not to have documented it either. It was an awesome little bar. My family is pretty open and we kept it from going too far in the gutter 😉