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24 Sep 2017


By Gracie Carroll

10 Surprisingly Chic Places To Visit In Rockland Maine

By Gracie Carroll

Gracie Carroll - Chic Places To Go Rockland Maine

Roadtrippin’, backpackin’, resort relaxin’… when it comes to travel, I’m pretty much down to go any where, any time. This¬†laissez-faire attitude lead to a very quick“HELL, YEAH.”¬†when my friend Catherine of Do The Daniel¬†asked if I’d be interested in joining her¬†on a sailing cruise¬†in Maine.

Never having sailed before, or been on a cruise, my mind couldn’t help but immediately imagine life on a large cruise ship “sailing around” the coast of Maine for a week. The reality of the journey¬†we were about to embark on, however, was a little different. Catherine sent me a link to a week at sea on the Maine Windjammer¬†J&E Riggin , and my eyes and mind quickly adjusted from the imaginary hotel-like cruise ship to a (real life)¬†legendary 90-year-old, 98- foot-long schooner.

My initial thoughts were, “Where exactly do we sleep!?” and “What do we do all day on the boat? No spa!?”; I quickly reeled myself back in and opened myself up to a completely new experience, one I knew I could not only endure, but enjoy too. Plus, Catherine is a Millennial Granny just like me, so I knew we would relish in the art of doing nothing together over the course of our trip.

Our week at sea departed from the sleepy (and tiny) town of Rockland, Maine, which we got to via  a convenient and quick direct Porter flight to Boston, followed by a flight on Cape Air that got us to the local airport, a mere 10 minute drive away from town.


Catherine and I we were the only passengers on this 9-seater Cape Air plane!

With only a quick stay in Rockland on our way in and out (before and after our week at sea, obvi), I was surprised to find a number of surprisingly chic places to visit in Rockland that spanned the total of their *very approximately* six-block main street, that’s literally called Main Street.

See below for a little more on our experience on the J&E Riggin (more to come!) and the super chic, and very noteworthy, spots we found during our brief stay in Rockland, Maine that you gotta visit:

Maine Windjammer J&E Riggin

Maine Windjammer J&E Riggin Schooner

If you’re having a hard time picturing the 90-year-old ship we lived on for four days,¬†the image above does a good job of showing you exactly what it looks like. It’s massive, and beautiful, although still a wonder how it can actually sleep over twenty guests. Visit this page on their site for a better idea of the accommodations. Even though the beds are small and¬†the sleeping environment can feel a bit like camping, the team is right in that it truly doesn’t matter because the only time you’re in your room is to, well, sleep. The majority of your day is spent out on deck relaxing, looking out at the incredible views, feasting on the amazing spread by CIA-trained Chef Annie Mahle (who happens to be the wife and business partner of Captain Jon), and getting to know your fellow schooner passengers and crew.

I joked that our trip on the Maine Windjammer J&E Riggin was a rather unexpected Digital Detox (there was literally no wifi and hardly and data service during the trip), which sent me into a serious panic at first, but was probably my favourite part about the trip by the end. It forced me to put my phone and computer down and soak in every moment of the amazing trip, without trying to “experience” it though a screen. Sailing like this is truly incredible and I would highly recommend it to anyone who is up for a different type of vacation. Catherine and I are already planning our return next summer!

Cafe Miranda

As mentioned above, when we got to the boat on Sunday evening, I was sent into a panic when we were¬†told that we¬†wouldn’t¬†have access to the internet for, possibly, the next four days. As soon as the welcome¬†“Captain’s Call” ended, Catherine and I immediately ran from the boat into town to try and find a wifi connection before the end of the night — no easy feat when only a few businesses have free wifi and everything shuts down early.¬†Our hunt lead us to an adorable restaurant called Cafe Miranda that not only had food and free wifi , but a pink flamingo decor theme and a bathroom decorated in Elvis photos. All major wins in my books! If you’re wondering what this flamingo neon light has to do with it, it’s the one featured on the wall of their patio that I instantly fell in love with.¬† Whether you’re looking for a wifi connection or not, go to Cafe Miranda.

250 Main Hotel

Since we slept on the boat¬†for our first night in Rockland (after dinner at Cafe Miranda) and then set sail the next morning, we didn’t get back to town until the following Thursday. When we were back on land, we were lucky enough to stay the night at the super new, super modern and super chic 250 Main Hotel — the tallest building in Rockland (from what Captain told me). This hotel is like staying in an art gallery, and instantly had me feeling as though I was staying in a boutique hotel in New York City or Los Angeles rather than a teeny tiny town in Maine. Catherine and I shared a spacious room with two incredible comfy queen beds and that had an amazing view overlooking the water. We were also extremely happy to be invited to their early evening “Wine Social” where we were treated to crisp glasses of¬†ros√© and a selection of tasty cheese to enjoy on the house. 250 Main Hotel, we love you!

Rock City Coffee Roasters

Rock City Coffee Roasters has got the town of Rockland on lock. Anywhere you go in this town, they will be serving Rock City Coffee. And why wouldn’t they? These delicious coffee beans are roasted right there in town — we even had Rock City Coffee on the boat! We started every day that we were in Rockland at the OG Rock City Coffee Roasters location on Main Street that is conveniently located right next to 250 Main Hotel. The wooden fence to the left of the Rock City Coffee entrance in the photo above? That’s where the hotel now lives. If you’re looking for great coffee and a great souvenir to bring back, make it a bag of Rock City Coffee Roasters coffee beans.

Periscope Shop

Rockland is a funny place. Just when you think you’ve seen all of the typical souvenir and small town fashion shops, you stumble upon a place that is so epicly chic you are legitimately confused as to how¬†such a place could exist in such a small town. After falling head over heals for 250 Main Hotel we truly didn’t think there was anything else like it in Rockland. When we walked by the Periscope Shop along the main strip, we literally did a double take before walking in. But oh were we glad that we did. Filled with incredible Scandinavian furniture and home wares, this beautiful shop is what #homegoals are made of. Since I couldn’t possibly bring any major pieces with me, I purchased a beautiful brass hairpin made locally in Montville, Maine. Even if it’s just to ogle the eye candy, do not miss the opportunity to step inside Periscope Shop.

Main Street Markets

Gracie Carroll Chic Places To Visit Rockland Maine

If you happened to catch my insta stories or this post while I was in Rockland, there’s a good chance you might have seen me share my excitement over¬†discovering ros√© in a can. Yes, that’s right,¬†ROSE¬†IN A CAN, PEOPLE! This magical unicorn filled with wine was discovered inside Main Street Markets — a super chic market that’s filled with beautiful fresh flowers, every gourmet ingredient you could ever dream of, and an adorable cafe/deli. For a healthy lunch, this is a fantastic spot where you can pop in to order a fresh salad, made-to-order smoothie, or choose from their uber yummy selection of hot foods. We loved this place so much that¬†Catherine and I went there for lunch two days in a row. We love Main Street Markets!


shop four twelve 412 rockland maine

Shop fourTWELVE is a super chic boutique on Main Street that Catherine and I both worked very hard to avoid during our stay. Why? Because we knew it would be the type of place where we could easily max out our credit cards and find it rather challenging to fit any of our buys into our already-over-stuffed carry on bags. After one last run along the main shopping strip (aka Main Street, ha!)¬†to double check I had all the best spots for this list, I popped in on my own to take a look, up close and personal. We were right, I determined within a matter of seconds, we would have totally wanted to buy everything in their shop.¬†The first thing I spotted upon entering was a stack of beautiful cashmere sweaters by my favourite Demylee, an adorable cropped and distressed jean jacket by Mother Denim was hanging on the wall, and there were a pair of classic black Swedish Hasbeens booties right in front of me — wardrobe heaven! I loved everything about the laid back, cool and slightly boho but seriously chic vibes of fourTWELVE.

In Good Company

On our first night in Rockland, Captain and Annie shared a list of their favourite restaurants in town with everyone on board, and encouraged us all to go out for dinner before we set sail.¬†Although we found ourselves at Cafe Miranda that night (for the wifi), we took note of Cap and Annie’s mention of¬†In Good Company being their favourite restaurant in town. We decided that¬†we would reserve our visit for our last night in Rockland (upon our return) and we were so glad we did. This cozy little restaurant feels like eating in a friend’s home — a perfect spot for indulging in some wine and a fresh but hearty meal. Our Captain shared that he always orders the beef tenderloin and we can now confirm that it is awesome.

Curator Men’s Consignment

curator men's consignment

Although there are quite a few second hand shops along the shopping strip in Rockland, none are curated like Curator Men’s Consignment. Passing by, we noted it said “men’s” on the sign, as well as the fully clad female mannequin in the window. Clearly they had some women’s clothing inside, so we ventured in. Even with just one rolling rack dedicated to women’s clothing, I had no trouble finding items to buy and left with an amazing silk bias-cut dress that was priced at¬†just $28. Gals and guys, don’t sleep on visiting Curator Men’s Consignment.

The Lobster Shack

Last but not least on this list is The Lobster Shack. Ah, The Lobster Shack! I knew I loved it the moment I laid eyes on this adorable little cottage that hides at the end of a little garden just off Main Street. Catherine and I challenged ourselves to finding the best lobster roll during our trip, and although she had tapped out by this point, I could not leave Rockland without trying a lobster roll from The Lobster Shack. As my face in the photo above my tell you, I’m happy¬†I did! This might have honestly been my favourite from the trip. Not only was it piled with lobster and super fresh, but it came with a side of chips and a yummy thai-style coleslaw for just $17 (all other lobster rolls we had in Boston were $25 each or more with no extra sides). When we left, I noticed their sign out front said that they were voted ‘Best Lobster Roll’ by the Boston Globe. Obviously, I wasn’t surprised.


If you’re heading to Rockland, enjoy! We loved it.




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