I recently did a long weekend solo trip to Rockport, Massachusetts and had an amazing time! From beautiful sunsets and coastal views to local lobster snacks to local art galleries to an overall relaxed vibe it was a great trip for inspiration and to unplug into nature and enjoy a slower pace.
Why Rockport?
For a while I have been researching a possible trip to the Bahamas or an island cruise for a solo getaway. I still want to take this trip, but a few months ago out of the blue I started reminiscing about a road trip my family took around 40 years ago (!) where one of our stops was Rockport, MA. I remembered seeing the rocky coastline, staying at some type of bed and breakfast or lodge, eating lobster on the street out of a paper container, and enjoying a hot chocolate with whipped creme and a strudel. As a child, I was particularly fascinated by the lobsters. Generally, I've been more a fan of beaches and tropical places (and Paris) for travel but couldn't get this memory out of my head after it popped up. We made albums/journals for each of our road trips (we did 3 big ones), but I looked in my old files at my house and couldn't find one for this trip. I called my mom, and she confirmed we went to Rockport MA (not Rockport ME). We had fun sharing memories. In the following weeks, I kept wondering whether it would still hold the same charm for me as an adult. Then it occurred to me - why not go and find out?
An Amazing Trip!
The trip was everything I hoped it would be. Rockport lived up to my memories, and as an adult I found new reasons to enjoy the visit. The town is so charming! It is very walkable with beautiful scenery, and there are art galleries throughout the town showcasing the works of local artists. My painting is inspired by sunsets and oceans, and I can see why artists would flock to Rockport for inspiration and choose to live there. Before my trip was over, I could imagine myself years down the road living in a small coastal town spending my time writing and painting and running a small gallery.
How to Get There
While it may feel a bit like Planes, Trains and Automobiles, you can easily get to Rockport by flying in to Boston and then taking a scenic train ride all the way to Rockport while seeing Salem, Gloucester, and other nearby cities along the way. There is no need to rent a car. I didn't need a car and was glad not to have to worry about renting or driving. A tip: Don't do like me and "wing it" once you get to the airport. Instead, confirm logistics beforehand to have an idea what to expect before landing. I (wrongly) assumed the train would depart from the airport, but in reality you have to take a couple of buses (or an Uber) to get to the Chelsea bus stop which is steps away from the Rockport commuter rail line. The train ride was $12.95 to Rockport and there are discounted weekend passes - what a deal!
Where to Stay
For accommodations, I was thoroughly satisfied with my decision to stay in Bearskin Neck and would stay in this part of Rockport again in a heartbeat. Bearskin Neck is in the center of the action and walking distance to almost anything you may want to see or do in Rockport. I got an oceanfront room at the Bearskin Neck Motor Lodge in the heart of downtown Rockport. The lodge sits right over the ocean with beautiful views and everything you need for comfortable lodging. Next door is a cute oceanfront deck bar called The Hideaway which unfortunately was closed during my trip due to weather. I was there in off-season (after Labor Day) and many places were closed for the season.
What to Do
Rockport is a charming town perfect for walking around to take in the sights. In Bearskin Neck, there are several blocks with clusters of local shops, art galleries, and restaurants. There are talented local artists with works ranging from abstract to portrait. While walking around, a must-do is stopping by Motif #1 (a historic red fishing shack) for a photo. An interesting fact - Motif #1 is the most painted building in the world!
Within walking distance of downtown Rockport and Bearskin Neck is The Headlands. It is worth a visit. A footpath leads to a vantage point of large granite rocks overlooking the harbor with views of the Bearskin Neck breakway and ocean. This would be a nice place for sunrise or sunset photos.
The Bearskin breakaway is the tip of the peninsula and you can walk out across the granite rocks to the center of the harbor. There are signs warning to walk at your own risk, but it is very doable as long as you take your time and wear appropriate shoes. This was one of my favorite spots for sunset photos. An added bonus is the number of sea gulls and birds that hang out and are quite docile for picture taking.
I also enjoyed walking onto Front Beach and Back Beach and around the shoreline. There were several people heading out to scuba dive in the ocean even in November!
For live entertainment performances, you can check out the schedule for the beautiful Shalin Liu Performance Center. It's located in the midst of local shops and galleries with views of the ocean through large windows behind the performance stage.
More Sunset Photos
Where to Dine
Note: things get quiet rather early in the evening in Rockport, particularly in the off season. You may need to plan an earlier dinner than normal. I enjoyed focusing on lunch and then for dinner either getting something smaller (or possibly a glass of wine) and then having something in my room while I relaxed. Part of the reason for my trip was to devote time to writing so I enjoyed having downtime. There is a great market near the train stop at the Whistlestop Mall which has some of everything, including snacks, meal options, wine and beer. I enjoyed having some food and beverages to enjoy on my balcony watching the sunset and having a leisure night after walking around all day.
A must do if you like seafood is ordering a lobster roll or boiled lobster from Roy Moore Lobster Company. They catch and serve local seafood. Going here was one of the very first things I did, and it was a bit of fate that the shop was located steps away from my lodge! You can order and take away or enjoy on the picnic tables facing the wharf behind the shop and enjoy a local craft beer while eating your lobster. The staff is friendly and helpful in navigating the menu options and specialties.
For breakfast/brunch, I tried two cafes which were both enjoyable - The Bean & Leaf Cafe and Brothers Brew Coffee Shop. The Bean & Leaf Cafe has tables with amazing ocean views and a relaxing atmosphere which was perfect for my writing. I enjoyed my blueberry sconce and cafe au lait, but the best thing about this cafe was the views and relaxing atmosphere. Brothers Brew was so friendly and comfortable, and my goodness the homemade donuts are to die for! It was probably a good thing I tried this cafe second as donuts are my weakness! They also have a restaurant on site that is open certain hours with ocean views.
For lunch/dinner, I had a fantastic lunch meal at My Place by the Sea on the water near the Bearskin Neck breakaway. The ocean views were amazing, and the service was friendly and attentive. I had a Guavarita margarita that was divine, and a hot chicken and brie baguette with side salad that was amazing. I also enjoyed a dinner at Feather & Wedge in Rockport which is a very classy, upscale restaurant and bar and one of the few places in town that stays open later in the evening. It was comfortable dining solo at both locations. I highly recommend both restaurants.
I ventured out on the train for lunch in Gloucester one afternoon specifically to dine at Seaport Grille on the water. I had an oceanview table, and a friendly bird outside watched me eat most of my meal! My meal was fantastic - grilled halibut from the harbor with parmesan crusted asparagus and a bloody mary. It was interesting to see Gloucester briefly in comparison to Rockport. I was glad I was staying in Rockport as I preferred it much more as a destination.
Final Thoughts
I am so glad I went with my gut and did a different type of vacation. I enjoyed seeing New England in a different way as an adult and the historical aspects of the area. I would definitely go back to Rockport. Also, the trip was inspiring and left me in a relaxed state of being with renewed goals. I wrote a lot while I was there and have continued writing since I returned. I also did a painting for the first time in months after returning, and I have a painting in mind to do in the future based on one of the sunsets I saw. I call that a successful long weekend trip!
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