Cape Cod & the Islands

Cape Cod, Martha’s Vineyard, Nantucket. They are the places of summer lore, filled with natural coastal beauty and the famous cedar-shingled cottages grayed to perfection, surrounded by blue hydrangeas and climbing roses. Visited by the presidents and celebrities who hob nob alongside the rest of us plebes, it is a destination for everyone.

Cape Cod, or “the Cape”, is accessed via the two bridges spanning the Cape Cod Canal from the Massachusetts mainland, and is bisected along its length via Route 6 from the Sagamore Bridge to the very tip of the Cape in Provincetown. Route 6a shadows Route 6 through the quieter, charming bay side, until it meets back up with Route 6 in Orleans. From the Bourne Bridge, on the southern end of the canal, Route 28 heads south to Falmouth, then curves east along the southern shore before joining up with Route 6 in Orleans.

The Cape’s shape resembles a flexed arm and has long been used to indicate where something is. The Outer Cape (from elbow to fist), is known for the Cape Cod National Seashore and Provincetown, the charming and long-time LGBTQ-friendly town, full of galleries and boutiques. The Outer Cape is for nature-lovers and those seeking a quieter sojourn. The ocean side is rougher and colder than the calmer waters of Cape Cod Bay to the west.

The Lower Cape (elbow) hosts Orleans, Harwich, Brewster and Chatham and forms a sort of a transition point between the quiet of the Outer Cape and the busier on the Mid-Cape. It is decidedly upscale, and Chatham is the perfect little spot for some boutique shopping and dining.

Mid-Cape (the upper arm) is where you find the towns of Dennis, Yarmouth and Barnstable and their various villages like Hyannis, Barnstable Village and Centerville. These towns span from the bay side to the southern shore. If you want quiet and charm, stay north. If you want fun in the sun, mini-golf, resorts and touristy shops, head south. The beaches on the southern side, on Nantucket Sound, are relatively calm and warm – great for families.

The Upper Cape (the shoulder and, ahem, the armpit) consists of Mashpee, Falmouth, Bourne and Sandwich and is closest to the mainland. Falmouth is famous for Wood’s Hole Oceanographic Center and its pretty downtown area, and Sandwich, despite being an entrance town to the Cape, is pretty and uncrowded and worth visiting for its own sake.

Martha’s Vineyard and Nantucket are accessed via ferries from Falmouth, Hyannis. Martha’s Vineyard is the closest and its main draws for visitors are Oak Bluffs, the primary ferry landing point, and Edgartown further south, both considered “down island”. Oak Bluffs is most famous for its colorful “gingerbread” cottages and younger vibe, while Edgartown is more staid, full of white clapboard captain’s homes and brick sidewalks. Further afield, “up island”, are the quiet and lovely towns of Chilmark, Menemsha and Aquinnah, the latter known for its famous cliffs and Gay Head Light.

Nantucket, last on our list, but hardly least, is further out to sea and its history is steeped in whaling, which you can learn about at the Whaling Museum. Perhaps the most charming (do I keep saying “charming”?) of the entire region, it is also the most isolated. But if you like cobblestone streets filled with restaurants and boutique shops, weathered, shingled homes, and endless beaches, this is your place. Not permanently, though, unless you are wealthy.

If there’s one thing to take away from all this, it’s that there are beaches throughout this region. Beautiful beaches. And sand dunes. Harbors, lighthouses and wharves. Sailing is a serious thing here. And fishing and whale watching. 

If you stay for the summer, you can visit the whole of the Cape and islands at your leisure, and spend some time on the water. Better yet, make a plan to come back every year, even just for a few days.