A New England fall getaway

By Amy Lynn O’Connell

I used to think that New England was reserved for wealthy, J. Crew model-type co-eds and women named Fifi carrying dogs named Muffy. “Oh Charles, more Chambord, please, and do tell the girls they have tennis lessons precisely at 5 p.m. I won’t have them losing to Foxcroft again.” Note: This is the appropriate moment for you to roll your eyes.

Stuffy archetypes do exist in the colonial states, but the region is far more accessible, affordable and relaxed than you may think. It’s funny how stereotypes get engrained in us, but it’s oh-so-fantastic to have the opportunity to put those stereotypes to the test and learn something new. Without bursting chords of communication theory, I’ll help you change your tune on New England with a few surprisingly simple ways to spend the end of your summer. Grab your sweater vest and sailing skills; we’re off to the tiny towns of northern New England for an unforgettable fall getaway.

If the sign says Peabody, don’t say it phonetically.

You’ve been like a skipping rock up the east coast – skimming the surface of each city before moving on to the next. After days in Boston, you decide it’s time to quiet some of the noise and spend a few days on the North Shore and maybe wander into Maine. Thankfully, a bit of charm landed you an upgrade on the rental car, and there’s just enough sunshine in the season for a convertible. First stop: Salem, MA.

Halloween is just around the corner, one of your favorite holidays! The fog of the short windy drive makes it hard to recall what you were last year, until you laugh at the thought of how tight those pants were. Famous for the witch trials, this little town greets you with a sign bragging “Founded 1626,” and the beautifully old buildings are evidence of the history. Google pulls up a couple creepy tales, and your companion shutters and squirms as you read them aloud. After picking up some special crystal trinkets from one of the modern witch shops near The Witch Museum, you settle down by the wharf for a bowl of creamy clam chowder. You consult a map and zoom off toward Rockport, MA, and the tiny B&B you’ve reserved. Rockport delivers every bit of charm you’d expect from a small New England town. The harbor is full of boats headed out early for happy hour at sea, and quaint shops sell handmade jewelry and home goods.

After checking into your cozy abode, you walk to the pier and see a golden retriever on the front of some college kid’s paddleboard – inspiring laughter and a photo op.  A couple kayaking follows the paddleboard, and somewhere in the distance fishermen line the rocks with lines cast into a dark abyss. On Tuna Wharf, you snag a pamphlet at the North Shore Kayak boat/board/bike rental shop and notice a corkboard posting from the recent Pride festival. Funny how so many small towns get a reputation for being close minded while here, pics of Pride are displayed next to a flyer for sewing lessons. Sweet. Settle into your small town skin, little progressive city dweller.

Dinner consists of a fresh fish sandwich and a couple Sam Adams seasonal brews on the 7th Wave rooftop. You laugh with a few locals and watch the boats jerk around in the breeze as the sun sets for the day. You breathe a sigh of relief and welcome an unfamiliar calm.

It’s morning, and the day is packed! A cheap plate of runny eggs at Red Skiff is followed by a premeditated bike rental. The squeaky old wheels carry you down to the water, through tall grass, and past behemoth homes with crow nests overlooking lighthouses on distant islands. Accidentally cruising into a private drive, the owner of this mansion laughs welcomingly from her porch and suggests a secret path that will get you “right on the coast with a couple great shots of the town in the distance.” You end the day with a slice of sweet fudge and ditch the bike for your trip north. Next stop: Kennebunkport, ME.

The name of the town makes you chuckle a bit, but a co-worker with keen sailing skills suggested it, so you booked a little spot on the beach for a few days. An evening charter boat is reserved for you and your equally relaxed travel companion. After an hour and a half drive north, punctuated with curiosity-promoted stops, you’re ready to board a beautiful ship for wine, appetizers and sightseeing with a handful of others.

Waiting back at the beach house is a fridge full of steamed lobster. Waiting thousands of miles back home is a to-do list that’s irrelevant for the moment. Here, on a boat sailing in the Atlantic, is an unexpectedly warm atmosphere, the chill of fall and a sweater (vest?) to keep you warm.