Given that Cape Cod is basically one big sandbar surrounded by water, it is no secret that once the temperatures start dropping, the crowds start to dissipate as well. This is especially true for the communities further out on the Lower Cape where many of the bustling seaside shacks along Route 6 are locked up and dark this time of year. And this is also the case for a number of dining and drinking spots in Provincetown, even though this charming community at the end of the peninsula retains at least some of its population as the winter approaches. A handful of options do remain open deep into the fall and winter (and some remain open all year long), and they run the gamut from romantic restaurants to old-school watering holes.
Starting in the charming and artsy-feeling East End, a must for couples and people who love cozy spots is Ciro & Sal's (4 Kiley Court), a tough-to-find restaurant just off Commercial Street at the end of a dead-end road. Northern Italian fare is front and center here (including pasta with butter sauce, pesto, Veal Milanese, and shrimp broiled in butter), and its fireplace, candlelit tables, exposed brick, and low ceilings make for a perfect date-night spot.
Further up Commercial are some interesting drinking establishments, and few are more scenic than the Harbor Lounge (359 Commercial Street), which sits at the end of a walkway and has sweeping views of Cape Cod Bay—and a pier accessed through a back door affords even more jaw-dropping views as well. If you’d rather stay warm, the comfy interior includes couches where you can stretch out, but keep in mind that no food is served here, so it’s more of a pre- or post-dinner place—and it tends to close for the season after the holidays, so call ahead.
A short distance west of Harbor Lounge is the Governor Bradford Restaurant (312 Commercial Street), a spacious and at-times wild spot in the summer that features an attractive old bar, plenty of seating in the dining area, and some very entertaining drag karaoke. During the colder months, the Governor Bradford is a warm and welcoming place to belly up to the bar for a drink and perhaps some pub grub such as clam chowder, broiled scallops, and burgers.
The Governor Bradford sits kitty corner from MacMillan Pier, which forms the border between the East End and the West End, the latter of which can be mobbed during the summer and is great for people-watching. Restaurants and bars abound on this stretch of Commercial, with one of the best year-round choices being The Canteen (225 Commercial Street), a friendly and funky eatery that feels like a laid-back California beach spot—and which features an outdoor area with gorgeous water views. Lobster rolls, fish and chips, oysters, and tropical-themed cocktails are offered here, and The Canteen actually morphs into a chalet-style restaurant during the holidays, complete with comfort food, hot beverages, and a fire pit.
Beer lovers have a good option across from The Canteen in the 1620 Brewhouse (214 Commercial Street), and while it is known for its great outdoor patio in the summer, the interior has plenty of room for seating at high-tops and at the bar. Some of the best burgers in town can be found here, and an assortment of regional craft beers are offered along with classic and modern cocktails.
Most dining and drinking options in Provincetown are found in the East End and West End, but one of the best restaurants in town is in neither, instead being in a rather generic-looking area away from the water near Route 6. But you shouldn’t overlook Mac's Fish House (85 Shank Painter Road), as it is a sleek and modern spot with raw bar items, sushi, a marvelous clam chowder, and a codfish sandwich that is about as fresh-tasting as you can get.
It seems that few people think all that much about Cape Cod after Labor Day, and that’s a shame because there is still plenty to see and do after the beaches clear out. And Provincetown is one of the best places on the Cape to visit during the off-season, especially since a good number of inns, shops, galleries, and yes, restaurants and bars continue to stay in operation as the cold air settles in.