Keepin’ It Short in Freeport 🥾

Trip with me and my husband on our adventures together!

A travel guide to help you with tips, places to visit, good global eats and anything else that comes with taking a trip away…. let’s start the trippin’!

Over the Memorial Day Weekend, my husband and I decided to take a lil itty bitty overnight trip to Freeport Maine https://www.visitfreeport.com/. We always like to take spontaneous road trips and love to expand our adventurous side, so I was all for this little one night getaway that my husband suggested, to celebrate the long holiday weekend. I never heard of Freeport nor knew anything it was known for, so I was in for a treat.  About a 2 hour drive from where we live, we left early enough so we could enjoy some of what this quaint town had to offer.  

On the way, once we crossed into the Maine state border, we stopped at a Starbucks at a highway rest stop so we could grab a quick, on the go, bite to eat…..and coffee. We needed that coffee pick me up for that long drive lol. We arrived around 11ish which was too early to check into our hotel, so we decided to head straight on over to what Freeport is known for, the LLBean Headquarters https://www.llbean.com/llb/shop/1000001705?page=store-flagship. Oh My Goodness. This place is HUGE! Over several blocks’ radius, this place is the mecca of all meccas for all those outdoorsy junkies (which we are not….hey, what can I say?, we’re city folk, but we had to check out this place since it was one thing to do in Freeport). This store, if you can even call it that, more like a complex, is your one stop shop for all your outdoorsy needs. First floor consisted of men’s clothing as well as gear for all types of fishing, hunting and camping tools, equipment & accessories. Oh, and a whole gun section which we were kind of shocked to see. We totally got it. We’re in Maine, where hunting is a big thing to do but we’re definitely not used to seeing that in any stores in the city. We knew we were in unfamiliar territory. That was an eye opener. Anyway, back to the store. 

The second floor consisted of the children and women’s clothing. This place was so big, they even had a wall to wall aquarium from one part of the store to the next, where you can sit inside a globe shaped dome where it looked like you were swimming among the salmon and fish that were in the tank. Picture worthy of course, especially for the kids. It was mostly meant for the kids since the space was not adult friendly, but I squeezed my way in there pretending I was five years old again lol. And of course, there were the ‘prized’ hunted animals, that not only curated the walls, but were displayed around the store like ‘models’ to entice customers that this is what you can get when you hunt in Maine. Something PETA would definitely frown upon. Again, I’m a city girl so seeing these life-like animals to me while walking around the store, made it all to real, that if I was ever stuck in the woods, I could come across these scary looking creatures.   

After checking this popular Freeport shopping attraction, we decided to get in our car and head on over to the main street where there were more shops to check out. We parked on one of the side streets in the free parking lot which was nice since parking can cost a lot depending on where you are. Since it was Sunday and the weather was beautiful, there were people walking around window shopping, eating outside at several restaurants and/or hanging out on one of the street benches listening to a solo performer singing his pretty little heart out while the beat in the background helped him with the notes. On our walk down Main Street discovering what other shops Freeport had to offer, we stopped to hear the performer sing, danced a little to the current song he was singing and gave him a tip for his bravato, confidence and his enjoyable performance. 

We hit up a Sperry, https://www.sperry.com/en/home, store right on Main and I bought a really comfy pair of sandals as well as a a pair of the famous Sperry boat shoes since I had to throw my other ones out because of many years of wear and tear. Because it was Memorial Day, all the stores were having a lot of deals, so I was happy I got my Sperry’s at a discounted price. Call me the bargain shopper I guess lol. There were a couple of other stores on Main Street that were also worth mentioning going into like the Mangy Moose, https://www.facebook.com/mangymoosemaine/, a gift shop that sells everything from apparel, home decor, books, kitchenware, accessories, toys, and of course, everything, moose-y. You name it, they have it. I always feel like these little towns always have a store like this, that has a tremendous variety of knick knacks ranging from clothing to home goods. Anyway, check this place out. It’s got a lot of great products & gifts to choose from.

After all that walking around in the sun, we decided to grab a bite to eat at a really busy Italian restaurant right on Main called Tuscan Brick Oven Bistro https://www.tuscanbrickovenbistro.com/. When looking up where to essentially go in Freeport, this popped up on the list for some great food and even better Bloody Mary’s! We decided to go here for lunch to see what all the talk was about. And we were so glad we did because the food was soooooooo GOOD! Of course I had to try a gourmet Bloody Mary that was garnished with pepperoncini, salami & mozzarella. Nothing like a little snack to literally go with your drink lol. It was definitely good, but a lil spicy for my liking. We literally ordered a bunch of apps + a pizza to share so we could have a little smorgasborg of food. 

We decided on the Maine Mussels app that were served with Polenta Frites, a Ceasar Salad, the Ultimate Caprese Brick Oven Pizza and a side of Herb and Truffle Dusted Hand-Cut Fries. Wow…..just WOW! My husband and I were fighting over the last mussel, that’s how good they were. The pizza was cooked to perfection, the fries were addicting as ever, and, honestly, I don’t think you could ever go wrong with a Ceasar. 

We wanted to digest our lunch a little bit and did a little more walking.  Another thing worth checking out at the end of Main, was a McDonald’s restaurant that was built within the same exact building that was standing on the property, which just happened to be a historical colonial home. McDonald’s, like any other fast food place has a certain look to it including the exterior. Obviously, it didn’t look like it should be a McDonald’s so it was a little weird to see such an eloquent building as a fast food joint. Not only is it in a historical 150 year-old building but just happens to be the town’s only McDonald’s, and the world’s fanciest, so it made the list of places to see when visiting Freeport. Check out this article in NewsWeek talking about the history behind this beloved restaurant in it’s unusual but welcoming environment……. https://www.newsweek.com/inside-mcdonalds-built-1850-mansion-fireplace-freeport-maine-1716152.

With all that salt we ate at lunch, we needed something sweet so we headed over to another ‘must see’ item on the Freeport list of things to do. Heading back towards where the shops were and close to where we parked, was a famous chocolate and candy shoppe called Wilbur’s of Maine, https://www.wilburs.com/, right off of Main Street. In business for over 40+ years, these chocolate connoisseurs know what people love….and one thing’s for sure, they LOVE chocolate!! Being a chocolate lover myself, you know I had to check this place out. And of course, buy a couple of truffles and chocolates to bring home to indulge in. If you have a sweet tooth like me, then you need to check this place out on your visit!

Side note: We also found out that the Wilbur’s Chocolate Factory, where all the store’s candies are made, was not too far from Main Street. The best part….. you can make an appointment to have a tour as well as make your own chocolate! Since we were on a limited stay this time around and because it was a holiday weekend, we didn’t get a chance to do this. Maybe on our next trip! 

At this point, we were done walking around Main Street for the day because there was one attraction we really wanted to check out. There was nothing like it around, it made you feel like you weren’t in Maine and the history with how it came about was pretty interesting. Plus, this was one of the MAIN places to see when visiting Freeport, so you know we were all about it. Enter: The Desert of Maine https://www.desertofmaine.com/.  I know what you’re thinking, there is no such thing as a desert in New England, nevermind in a coastal state. When I think of deserts, I automatically think of the Sahara Desert, and by all means, we were nowhere near Africa. So, I had to see this for myself.  At this point, it was around 3ish, which is when we could check in to our hotel, but we opted to go check out this attraction first and then head on over to our overnight abode. 

The Desert of Maine is a ’40 acre expanse of glacial sand dunes, surrounded by a coastal forest.’ According to its’ Wikipedia description, it’s not a ‘true desert’…..and it’s not man made either. According to theory, ‘nature laid it down and human error uncovered it.’ But how? Based on a write-up in Roadside America, ‘the Desert began as a giant prehistoric sand pile, blown here by Maine’s north winds after the last Ice Age, then gradually hidden beneath a thin layer of soil. In the 1860s sheep grazed the grass on top and ate down to the sand. A small patch appeared — and then the wind ripped it out of the ground and piled it into dunes. By the early 1900s the dunes were so high that they’d buried farm buildings and 50-foot-high trees. Henry Goldrup bought the land/farm and opened it as the Desert of Maine in 1926.’ And so, this popular attraction was born. 

Located at the dead end of a residential area on Desert Road, upon pulling into the parking lot, you see several trailers line the left side of the Welcome Center.  Not only is this an attraction, but a campground destination for the curious guests to back in their trailers or set up their tents https://www.desertofmaine.com/campground. New to 2022, the grounds built six cabins for guests to stay in as well. So plenty of options if you decide to sleep onsite.

On the right side of the Welcome Center, there was a site that was under construction called the Tuttle Barn. Heading into the Welcome Center/Gift Shop, we stopped at the admissions desk to pay for our entry which was $16 per adult ($12 for kids) & grabbed a map to help us navigate the grounds. Leaving the Welcome Center/Gift Shop, on the path leading to the Desert, there was a food & ice cream stand called Oasis, a mini golf course and a playground for kids. Then, you see the ‘desert’. Which again, looks very strange because there is so much sand that is lined with forest like pine trees, which the two don’t really go together when you think of a desert. It is really a rarity to see with your own eyes. 

There are stops to read the history about the site/farm/grounds while trekking in the sand. A good pair of sneakers is a must, along with some bug spray since you will be trekking in the forest too. If you decide to go in the warmer months, I suggest bringing some sunscreen, a hat and definitely a pair of sunglasses not only to keep the sun from your eyes but the sand if a wind gust comes thru. Along the sand dunes you will be walking on, there are paths off the dunes that lead you into the forest for some other activities to see like the ‘Gemstone Village’ (where you can pick your own gemstones), the ‘Vernal Pool’, the ‘Wishing Bridge’ & the ‘Roadside Attraction’…..an original 1920’s era Ford Model T. There’s a lot of walking and a lot to see. One of my favorite things was standing at the highest summit of the largest sand dunes at the desert and see a panoramic view of the whole grounds. It was so breathtaking! They had a seat for you to sit for a few just to take in the beauty of the scenery. 

We definitely did our walking for the day and after seeing everything this attraction had to offer, we grabbed an ice cream at Oasis for the road and headed to the Holiday Inn Express Suites,  https://www.ihg.com/holidayinnexpress/hotels/us/en/freeport/frept/hoteldetail, our hotel for the night. The hotel was in a perfect location, about a five to seven minute drive to Main Street. There are other hotels on the same street as ours, so to find a place to stay wouldn’t be a problem. We hung out at the hotel for a few, went to the pool, and got ready to grab a bite to eat for dinner. We wanted to keep it casual and wanted a place with t.v.’s since the Celtics were in the Playoffs and we wanted to watch the game. We heard that another place to check out for good eats on Lower Main Street was Gritty McDuff’s https://grittys.com/freeport-brew-pub/, your typical American bar fare and homemade beers with several big t.v.’s to watch a sports game. We started off with some wings and then dove right in to the Philly Cheesesteak and Reuben Sandwiches that we split. OMG, the sandwiches were some of the the BEST I’ve had!! Definitely check them out if you are in the area. Bonus, they have a huge deck with outdoor seating as well as a huge grassed area for the kids to run free on. At halftime, we decided to head out and call it a night since it was very looooooooooong day. 

The next morning we had the continental breakfast at our hotel, checked out and decided to go back to Main Street for a few other notable places to visit. Across the street from our hotel was the home of the Maine Beer Company https://mainebeercompany.com/beer/lunch, & since we sell it at my husband’s restaurant, he wanted to check it out. Come to find out, they were closed on Memorial Day, which we were totally bummed about and decided that we will def have to take another trip to Freeport to check it out. 

We headed down Main Street, parked in the same parking lot the day before (which was still free because of the holiday) and decided to check out the shops within the Freeport Village Station….outlet stores like we have in MA, like the Coach & Old Navy Outlet. We headed into a store called the Kitchen Outlet where I needed to grab a few things for our home, went into Old Navy because honestly, you can always find something in Old Navy, amiright?, and then into the Coach Outlet where I tried to persuade my husband that I needed a new bag when in actuality, I have too many. My husband won that battle and we kept it walking. We went into a store, more like a warehouse style loft space, called Freeport Market https://freeportmarket.me/, where there were all types of items from clothing & shoes, to accessories & jewelry, to decor & paintings……it was literally a plethora of products for the home or for you. The best part, all the products were handmade with tons of LOVE, from local Maine artisans & artists. I absolutely love that and of course had to support my fellow entrepreneurs. (We support & stick together, what can I say?) I found a really cute tray for my coffee table and my husband bought a snapback hat. Definitely check them out because there is a variety of cool, unique, one of a kind pieces that are handmade. And what better way to support small, local businesses than with an item that they created? I’m sure you can find something in here that you would love. 

After checking out all the businesses in the Freeport Market, we were getting a little hungry and decided to head on over to Linda Bean’s Maine Kitchen and Topside Tavern https://www.lindabeansperfectmaine.com/mainekitchen/restaurant/topside-tavern/, for some apps and some cold drinks. We ordered some Steamers, which are my fav, Calamari, and a Maine Haddock Melt Sandwich to split. The food was very satisfying and yummy. Definitely hit the spot. The restaurant has two floors and both floors have outdoor dining overlooking Main Street. It was too hot for us to eat outside, so we sat in the tavern dining room on the second floor. The seating on the second floor balcony seemed to be the most popular place to sit, eat and people watch below. 

Side note: If you don’t want a sit down restaurant to eat at, there was a food cart right at the entrance of the Freeport Village Station Shops, that sold Hot Dogs, Hamburgers, Lobster Rolls and cold drinks. We saw a lot of people getting the Lobster Rolls which seemed to be a big hit at this cart. There are some benches right next to the cart as well for you to sit on and eat your delicious roll. 

After eating, I wanted to check out a really cute boutique we passed the day before called Rustic Arrow https://rusticarrowmaine.com/, that sold the cutest clothes, accessories, jewelry, & home decor. Of course, being the fashionista that I am, I needed to see what they were all about. Their stuff was adorable! A little on the pricey side but well worth it. I ended up getting this really cute cream colored, palazzo pants set with a matching top.  Flowy, comfy and very summery is the look I was going for in this one. It came with a matching flowy top. Perfect for the hot weather. I also picked up a thick headband, intertwined with cream, beige & grey colors, that matched perfectly with my outfit. If you love fun and trendy clothing like I do, then this place is for you. Again, I’m sure you could find something to buy!

Having the sweet tooth that I do, we had to stop at Wicked Whoopies https://www.wickedwhoopies.com/, not too far from the Rustic arrow, which had the biggest whoopie pie selection I had ever seen. From Red Velvet, to Original, to Cookies and Cream, to Pumpkin, to Gingerbread to Banana Cream, they have EVERY type of flavor you could imagine. We picked up a Cookies & Cream and an Original Whoopie Pie for a lil snack on the way home. Oh my goodness, were those hella good!!! Just writing about them is making my mouth water lol. 

One last thing we had to do before leaving Main Street was to check out When Pigs Fly Breads https://sendbread.com/, located at the beginning of Main Street, before all the shops. They used to have a location in my hometown and I remember going in and grabbing some of their bread which was out of this world. So, I knew I wanted to check this one out. And of course, we had to bring some bread home too. Not only do they sell bread, but also jams, spreads, oils cookies & goodies. We chose the Baby Spinach, Onion and Garlic Ciabatta, Sun-dried Tomato & Fresh Basil Oil Artisan Bread and the Sourdough Classic Bread. The best part, they slice it right there for you on the spot, no extra charge. Make sure to grab a loaf when you’re checking out Main Street. 

Before heading home, there was one thing left on the ‘must see sights’ in Freeport and that was the Casco Castle https://meandermaine.com/place/casco-castle/. Not much of a castle presently, except for one, lone standing tower, situated in someone’s backyard. Which means you can’t visit this tower or even come near it, considering it is on private property. But you can see it from a narrow, residential road. Once an amusement park with a zoo and 100 room hotel from the early 1900’s overlooking Casco Bay, it’s sight today is a mere but eerie one. Story goes that in 1903, with the new electric trolley system that rode from Boston to Bangor, came to Freeport, which allowed more people to the area to visit the new amusement park built by Amos Gerald. Gerald’s sole idea for this attraction was that people were required to use the electric trolley system to visit the grounds of the castle. Once the car was invented as a means of transportation in America, the electric trolley saw less and less action and eventually caused the castle to fall into financial trouble. Gerald tried to keep it going for as long as he could until unfortunately, in 1914, the castle suffered a fire which burned the castle to the ground…..except for the stone tower, which still stands today. Pretty cool to see a part of a castle especially when it is surrounded by houses. And the history behind it makes it that much cooler to see. Some people say the best view of the castle is on the bay but if you are driving it’s def worth a peek. Take a pic from the road and remember, don’t trespass!

Last attraction with its history lesson was a good way to end this trip. All in all, we had a blast in Freeport! Who knew this little town even existed? So glad we got to check out some cool spots, try some yummy eats and learned some history on this 24 hour trip to Maine!

Hope you enjoyed what I shared with you!! If you are visiting and have questions, don’t hesitate to ask me with either a comment below or send me an email!

Check back for our next trippin’ adventure!

Until the next trip with us!!