It's our fourth edition of Gothamist's travel content, Gothamist Getaways. A few times a year, we'll have a week of posts featuring looks at travel, food, products and tips—near and far—for making your trips more enjoyable. So sit back, dream of your next journey and let us know if you have any hints for us—email

Halibut Point State Park (Barry G./Foursquare)

The 60-something mile stretch where route 1A hugs northern Massachusetts, clips New Hampshire and meanders into Maine is a magical trail of craggy seascapes, dotted with manses that beg to inspire opulent ghost stories. This trifecta of seaside towns—Rockport, MA, Portsmouth, NH and Kittery, ME—make for a sweet 6-7 hour sojourn from New York, filled with quaint inns, great eats and vibrant artist colonies well worth exploring over a long weekend.


About 40 miles north of Boston, Rockport sits on the tip of the Cape Ann peninsula, an idyllic seaside town where lobster fisherman mix and mingle with local artists. No trip to this neck of the woods would be complete without clam chowder and a lobster roll at Lobstaland, a tasty year-round seafood spot in nearby Gloucester.

Lobstaland (Joe C./Foursquare)

Grab a cup of coffee and exotic donut (think maple bacon!) at the Brother's Brew Coffee Shop while cruising Bearskin Neck's cute little shops, art galleries and restaurants. Cruise over to neighboring Gloucester for a hike in Halibut Point State Park, a breathtaking rocky park and bird conservation site loaded with tidal pools and flat trails for cross-country skiing.

Emerson Inn (Facebook)

To crash, stay at the recently renovated Emerson Inn by the Sea and soak in the beauty the beach offers in the dead of winter.


Meander down route 1A or zip up I-95 across the New Hampshire border to the arty town of Portsmouth. Warm up with a hearty breakfast at The Friendly Toast, they make amazing pancakes for both the gluttonous and gluten-free.

The Friendly Toast (Anson/Foursquare)

Check into the lovingly restored, locally-owned boutique Hotel Portsmouth, a gorgeous mansion with modern rooms and amenities just steps from Market Square. Off-season weekend rates begin at $149/night. Come February, a gallery/restaurant/performance space called 3SArtspace is due to open and is eagerly anticipated by locals. If you're around in summer, you can see what neighborhood artists are up to at The Button Factory, a local live/work space. If it's off-season, you can still check out Drift Gallery, a lovely space showing work by contemporary fine artists.

The Queen Suite at the Hotel Portsmouth (Facebook)

If you're in the mood for an upscale dinner, Cava Tapas and Wine Bar offers a variety of small plates, cheeses and larger dishes flavored with a Mediterranean influence.


You don't even have to check out of The Hotel Portsmouth - a quick walk or drive over the Memorial Bridge in Downtown Portsmouth will spit you out in Kittery, ME, the last stop on your arty New England tour. To soak in the scenery, park and stroll along Gerrish Island at Kittery Point, a park with walking trails along the scenic shoreline. Kittery's downtown area, known as "The Foreside" is in the midst of a revitalization, with galleries, shops and bakeries cropping up.

Gerrish Island (Alex F./Foursquare)

Art on the Hill, also known as the Wentworth Dennett Studios, plays host to a variety of artists and artisans, along with yoga and pilates classes. Owned by the same folks who preside over Robert's, Lil's Cafe is touted by locals as a great place to stop for a caffeine fix and a pastry. Be sure to swing by the Moira Walsh Gallery to view noteworthy contemporary work and for a bite to eat, you'll find a modern spin on local seafood, farm-to-table ingredients and local craft brews at Robert's Maine Grill.

Art on the Hill (Facebook)

Another hotspot is The Black Birch. Its gorgeous wooden bar is ideal to turn drinks and sophisticated bar snacks into dinner. Score some serious deals before the long drive back at the nearby Kittery Outlets, where you'll find all the usual-suspect stuff from big name stores to stock up on.

Vivian Manning-Schaffel is a journalist, copywriter and essayist who lives and works in Brooklyn, NY. Find her on Twitter @SoapboxDirty.