A few years ago, my friends and I realized that you can experience the same brand of fun that idols like Clarkson, Hammond, and May have on their epic road trips in your own back yard. That sparked an interest in local travel that we’ve been exploring ever since. I’m the planner/driver so I do a lot of scouting runs, like this one to the “Massachusetts Riviera” AKA Cape Ann, a rocky piece of coastal land just below the border between Massachusetts and New Hampshire:

Highway 127 runs along the coast and through the tidal planes of the cape. Along the way, 127 passes through Rockport and Gloucester, two classic New England seaside towns. Gloucester is the oldest port in the USA, founded just 3 years after Plymouth Colony, in 1623. Both are worth a visit.

Gloucester is more industrial in nature, though it does have a sizable downtown area with several blocks of restaurants and shops housed in historic buildings. Rockport is much smaller, but features a massive pier with a similar assortment of businesses. And between the two? State parks, gorgeous coastal properties, and beautiful vistas.


My first stop was Halibut Point State Park, a rocky New England beach with a rouge cliff adorning the seaside in one spot. Here’s the “point” in question from afar. It’s around 100 feet tall:

At this point, I should explain why I was driving around Massachusetts in the middle of the afternoon on a Tuesday: I was laid off recently. This scouting trip allowed for a bit of soul searching, especially down by the seashore. I carefully made my way to a spot by the water, sat down, and did a little ruminating for a bit.


I stumbled upon “Mini Stonehenge” on my walk back to the car. Props to whoever put time into this! I liked it.


Rockport is around 20 minutes of coastal highway away from the state park. It features two massive piers, one for parking plus another for shopping and eating. Visiting Massachusetts’ tourist-oriented coastal towns in the off season is dicey. Most of the business on the main pier were still closed, which was disappointing, as I’d arrived with an appetite and hoped to find something to eat. It’s always interesting to get a taste of local culture via investigating which businesses are open year-round. The only “restaurant” I found was a small crab shack with three items on the menu: boiled lobster, crab cakes, and fries. I decided to hold out for something in Gloucester.

One of two small streets on the pier. Everything you see here is closed! Judging by the handwritten signs I saw in most windows, I was exactly one week too early.

Gloucester doesn’t have the quaint fishing village atmosphere that tourists flock to Rockport fore. It’s a little rough around the edges. The waterfront isn’t as well-manicured because it’s used by fishermen and fish packing businesses. However, it’s also the home of Cape Ann Brewing Company, who operate a humble dockside brewpub that’s open year-round.


I can’t resist seafood or craft beer. The dining area featured a combination of long picnic table style seating and small booths. It’s communal, unpretentious atmosphere made me feel at home. This is definitely where the locals hang out. Young musicians played guitar and sang quietly at a booth in the back, and local sports lit up the bar via two widescreens behind the bar. I ordered fish and chips, an old standby. I’m always searching for the perfect fish and chips. And that’s exactly what I got! I HAVE to go back.

Perfection: fresh fish, strong beer batter, and judiciously seasoned fries.


After that? I slid into a gnarly food coma behind the wheel of the Q, and floated my way home. It was a perfect day and I’ll be back ASAP with my favorite people in tow.