Freeport & Portland (Maine)
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For one of my 30th birthday presents, Sarah surprised me by booking an Airbnb cottage in Freeport, Maine for the weekend. Over the course of the last few months, I had mentioned several times that I wanted to stay in a cabin somewhere in New Hampshire or Maine so it was really the perfect surprise and gift.  Not only was I able to cross something off my bucket list, but it was a chance to get away after a busy week at work. 

Bailiwick Cottage

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We left Boston on a Friday night and took the two and a half hour drive to Freeport, Maine. Unfortunately, we got in pretty late so there wasn't too much to do besides hang out in the cottage and rest up for the next day.  The cottage itself was beautiful. It was cozy, private and nicely designed with various colorful art pieces on the wall. 

The next day, we woke up and enjoyed the beautiful view of the woods and the frozen ocean from the window of the cottage. We got ready and headed into downtown Freeport, which was just a 15 minute drive from where we were staying. 

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Downtown Freeport

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If you know anything about Freeport, it's most likely that you know it's the home of L.L. Bean.  Although L.L. Bean is a big part of the town, it's not the only thing. Besides the popular outdoor and recreation clothing store, there are a host of other shopping outlets like Nike, The NorthFace, and Ralph Lauren as well as plenty of restaurants, giving you plenty of options of how you can spend your time and spend your money. 

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After checking out the area for a little while, we headed over to Isabella's Sticky Bun Cafe & Bakery. We originally planned to go to Linda Bean's Perfect Maine but it wasn't open yet. Not wanting to waste any time, we decided Isabella's Sticky Bun Cafe & Bakery sounded good. It ended up being the best decision we made all weekend. We both had their homemade Sticky Bun French Toast with bacon and agreed that it was one of the best things that we had ever eaten in our lives.  It was so delicious that I had even told the manager that we were going to come back the next morning to try the Sticky Bun Bacon, Egg, and Cheese sandwich. 

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Wolfe's Neck Woods State Park

With our bellies full, we took a short ride to Wolfe's Neck Woods State Park. The state park is right off the Casco Bay and the Harraseeket River.  It stretches over 200 arces and has a number of different hiking trails including the popular Casco Bay Trail, which we took.  

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The Casco Bay Trail was a relatively easy hike along the coast. There are a number of side trails off of it that provide access to the beach and ocean.  With the tide being out, we were able to walk on the rocks and roam around a little bit. 

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The views of the ocean and the surrounding islands were beautiful. The snow and the ice chunks in the ocean made it feel like we were in Alaska or somewhere much colder.  

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The trail eventually cuts into woods and loops back to the parking lot. During the latter parts of the trail, we saw a big tree that had tipped over. 

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Downtown Portland


Following a hour or so at Wolfe's Neck Woods State Park, we jumped back in the car and took a half hour trip to Portland. We walked around downtown Portland looking for a place to eat. We eventually decided on a local tavern, where we enjoyed a few beers and a pulled pork sandwich and burger respectively. It wasn't the greatest service but the people watching through the window made up for it. 

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Rising Tide Brewery 

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I had never heard of Rising Tide before, but we wanted to go to a brewery and their brewery was the closest one to us. Not only was the beer good, but there was a good, active crowd. We each got a flight to try out their array of craft beer and took a seat at a table. We played our favorite card game, Palace, and hung out for a bit before heading to mall and then back to Freeport.

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Before getting back to the cottage, we stopped at Bowstreetmarket for some drinks and food to snack on while hanging out for the rest of the night. 

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The next morning, we packed up and headed out with plans to go back to Isabella's Sticky Buns Cafe & Bakery for breakfast. But, we ended up having a big problem. It rained the night before and the roads were iced over so when I tried to drive up the hill to leave the cottage, my car started sliding back.

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After a handful of times trying to get my car from being stuck in the snow and even getting help from our Airbnb host and neighbors, we finally called AAA. An hour later, we were able to leave thanks to a AAA truck pulling my car up with chains. 

Fort Williams (Portland Head Light)

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Not wanting to end our trip like that, we stopped at Fort Williams in Cape Elizabeth. Fort Williams is home to Portland Head Light, arguably the most photographed lighthouse in the world. You can find the historc lighthouse featured in a number of calendars and on a number of posters. 

I'd been here before but this time around, the weather wasn't nice. It was raining and windy and there was a good amount of snow and ice but that didn't stop us from walking down to the ocean and exploring the coastline. 

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We snapped a few photos of the lighthouse, ocean, and the surrounding area before jumping back in the car and heading back home. 

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Overall, it was a really good weekend and nice way to celebrate a milestone birthday. My last few trips to Maine have really been enjoyable. I would have loved to have another day or so to explore more, but we got to do a little bit of everything in a short amount of time. Taking another trip to Freeport and Portland are both on my lists of things to do this upcoming summer. If you have any suggestions of things to do in Maine next time, please let me know by dropping a comment below!

For more, follow me on Instagram at @LindseyGamble_ and @TravelWithGamble