Woods Hole, Massachusetts

Coffee Obsession

Somewhere to sit it out

Coffee Obsession's Woods Hole shop sits on the corner of Water Street near the Steamship Authority, a handy place to grab a coffee and a quick bite before the ferry to the islands. It's the second location of a family-owned, independent coffee shop that started in Falmouth in 1992. Look for the oval blue sign on the shingled corner building; inside, breakfast and lunch are made to order and baristas pull specialty coffee drinks.

Landfall Restaurant

Somewhere to sit it out

Landfall sits right on Woods Hole Harbor on Luscombe Avenue, steps from the Steamship Authority ferry docks, serving fresh local seafood like lobster, swordfish, clams, scallops and seasonal fish. The dining room is built from wood taken from shipwrecks and boards from old buildings, with buoys, lobster pots and harpoons hung from the beams, and a seaside bar pours fresh-squeezed cocktails. Outside there's a brick patio under the big LANDFALL sign, Adirondack chairs against a buoy-covered fence, and a little clam shack window. The family-run restaurant has been here since 1946.

Masterson Made

Indoor activity

Masterson Made is a thoughtfully curated home decor, art, and gift shop in Woods Hole village, Falmouth. Owners Melissa and Patrick create woodwork on-site — handcrafted cutting boards and soy candles — alongside a carefully selected collection of coastal kitchenware, original artwork, and locally made goods. It's the kind of store where everything on the shelf has a story.

Quahog Republic Leeside Pub

Somewhere to sit it out

The Leeside Pub is the Woods Hole outpost of the Quahog Republic crew, set on Railroad Avenue directly across from the Steamship Authority ferry terminal. It's a natural stop before or after the boat: grab a burger and a Mai Tai and take in the ocean views and maritime feel. The shingled building with its navy awning and big lobster-claw sign is easy to spot from the ferry lot, and there's a dedicated event space with water views for groups. Seating is first-come, first-served.

Under the Sun

Indoor activity

Under the Sun is a cooperative gallery and boutique in Woods Hole village, showcasing handcrafted work by local and American artists — jewelry, ceramics, stained glass, wearables, photography, and unique gifts for the home. Everything on the shelves has been made by hand, giving the shop a distinct, artisan character you won't find in chain retail. A wonderful spot to find a truly one-of-a-kind keepsake from your time on the Cape.

Water Street Kitchen

Somewhere to sit it out

Water Street Kitchen is a dinner spot in a weathered shingle building right on the water at 56 Water Street in Woods Hole. Their menu changes with the seasons, made from scratch with global influences, and leans on locally and sustainably fished and farmed ingredients, with craft cocktails at the bar. Their own motto is "Food is Love," and the place aims to feel like the best home-cooked supper. Tables can be booked ahead.