Road Trip Weekend: Gloucester, Mass.

Welcome to Gloucester!

This past weekend I was lucky enough to celebrate my one year anniversary with my wonderful boyfriend. If you ask my boyfriend he would gladly recount the tale of the dark and stormy night we met 365 days ago. And to celebrate such an amazing and wonderful occasion, we headed north to Gloucester, MA to explore another part of our country. Taking road trips is one of our favorite ways to spend a weekend and, since my boyfriend has never been to the chilly north, Gloucester and other towns outside of Boston were our chosen destination for this excursion.

Gloucester has it’s claim to fame as being “America’s oldest seaport.” The exciting part, for me at least, is that it is still a functional seaport recalling both Mystic Pizza (set in Mystic Seaport in Connecticut) and The Perfect Storm, set right there in Gloucester (and they even have a tour to all the famous places from the movie and true story). We arrived on a beautiful sunny day and, while our bed and breakfast reminded me of staying in the aging colonial of a distant great aunt, we had a view of the harbor and the stacks of lobster traps and hauled in boats. While my boyfriend navigated the windy streets of the old sea village, I loved how simply rustic and beautiful it was.

Fisherman's Memorial

Though we stayed in Gloucester, that did not stop us from gassing up the Jetta and heading all over Cape Ann and other points just outside of Boston. One morning we ventured just 15 minutes up rte. 127 to Rockport. This is going to be my next vacation spot, after all the other places on our long and extensive list. It was even more old seaport-y than Gloucester and much more like Martha’s Vineyard (aka touristy). It was beautiful despite the cloudy weather; it just emphasized its New England-ness.

Boats in Rockport

Loving the Rockport bay


Town of Rockport

On our first and last days of the trip, we ventured into Salem. This was our original reason for picking Massachusetts. It’s handy and silly to have your anniversary fall just before Halloween (our second date was actually on Halloween last year complete with scary movies and handing out candy). Salem goes crazy for Halloween, though it’s pretty crazy for most of the rest of the year too. We saw lots of costumes, interesting locals and my wonderful boyfriend let me tour the House of Seven Gables. As my major in college was Historic Preservation, meaning I love old houses, I drooled over the woodwork, secret passageways and reproduction wallpaper. Not so happily, no photography was allowed inside.

The Bewitched Statue: my favorite witch!

The interesting Salem sights

House of the Seven Gables, Hawthorne's famous inspiration

On Sunday, we indulged being true historical tourists and traveled to Lexington and Concord. The starting point of the American Revolution, so basically the birthplace of our independence, we drove Paul Revere’s midnight ride and the advance of the British soldiers as they met the American Minute Men. We started at Lexington Battle Green and then drove to Minute Man National Park. We got a bit lost on the trail and I tried in vain to get my boyfriend to pretend he got shot by the re-enactor. Then we went to Concord where I got to visit Orchard House (well not really visit, see the outside because we didn’t have enough time for the 45 minute tour but someday!). My love of Louisa May Alcott and Little Women was partially satisfied. Then we traveled to the North Bridge where “the shot heard ’round the world” was fired. We also managed to squeeze a visit to Thoreau’s famous Walden Pond and Sleepy Hollow Cemetery at dusk into the trip. Of course we would visit a famously creepy cemetery at dusk. Good pictures though.

Lexington Battle Green

on the trail to independence

Orchard House, home of the Alcotts

North Bridge, infamously known for "the shot heard 'round the world"

Sleepy Hollow Cemetery

Since I am obsessed with food and good eats, I cannot neglect some of the great food and funky eateries we visited. On Sunday morning in Gloucester, we flipped through the phone book and picked a place called Sugar Magnolia’s. We happened to stumble upon the hot breakfast spot in town, especially for Sunday morning brunch. The definitely local eatery offered us seating at a bar and some of the most delicious food ever, including the boy’s cinnamon raisin french toast and my build-your-own omelette with delish potatoes. During our evening in Salem, we wandered aimlessly looking for something that wasn’t crowded by costumed tourists and found the Old Spot. Named after a rare breed of pig, I had a great curried chicken wrap and blueberry beer. Yes, blueberry beer, fantastic! And finally, another awesome restaurant we encountered on our travels was Rockafellas in Salem. Located in a former bank, they transformed the bank vault into a wine cellar and topped an old piano to make it into a high top table. The food was okay but you couldn’t beat the feeling of cool.

Sugar Mag's

The Old Spot


Our Massachusetts and first anniversary were definitely a success!

Happy Anniversary! Happy Massachusetts!


One thought on “Road Trip Weekend: Gloucester, Mass.

  1. Pingback: Another Adventure: Maryland’s Eastern Shore « The Lemonade Stand

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