The Beach Times

3 Great Places For Dinner on Osterville's Main Street
Posted by Kinlin Grover | Monday, July 20, 2020

When you book a vacation rental in Osterville, Massachusetts, you'll probably picture yourself lounging on Dowses Beach, taking a boat into Nantucket Sound, or exploring some of the village's historic sites.

You might also spend some time visiting the farmer's market, hiking the trails, and buying some souvenirs at the local shops.

But what about when it's time to eat?

Well, you're in luck because Osterville has one of Barnstable's most impressive dining scenes, with some of its trendy restaurants sitting along a small stretch of Main Street.

If you're spending an evening in the Main Street area, reserve a table at one of these high-end local eateries for a meal that you won't soon forget.

Wimpy's Seafood Cafe and Market

From the second you walk into Wimpy's, you'll know that you're in a quintessential Cape Cod seafood restaurant. 

This eatery, which first opened its doors in 1938, has all the local favorites, such as quahog chowder, oysters, scallops, lobster rolls, and fish dishes, on the menu. There's a raw bar here, as well, and tons of options for those looking for something other than seafood, including turkey and pot roast dinners.

Wimpy's is a large establishment that has an on-site pub offering live entertainment in the summer and has two fireplace rooms for a cozy meal with someone special. You can even grab some takeout from the market if you want to eat at your vacation rental.

You won't want to miss Wimpy's Seafood Cafe and Market on your Cape Cod vacation, but be sure to make a reservation because they're often busy.

Crisp Flatbread Inc.

Although its name might sound like its a takeaway restaurant, Crisp Flatbread is a full-service eatery with a bar, booth seating, and a diverse menu. Takeout is available down the street at Crisp Too Express, however, which is the original Crisp's sister restaurant.

As for the food, the flatbread options on the menu are some of the most popular, but you'll also find unique pasta dishes and a wide selection of salads. The flatbread is made with organic flour, and you can create your own pie using the dozens of ingredients they carry.

There's a significant snack menu at Crisp, as well, which features items like truffle fries, bacon & clams, spinach artichoke dip, grass-fed meatballs, and chicken wings.

Whether you're in the mood for a full dining experience or want to grab a quick bite to eat at your vacation rental, Crisp Flatbread's two locations on Osterville's Main Street have you covered.

Five Bays Bistro

The great thing about enjoying a meal at Five Bays Bistro is that you can make a night of it. The doors open at 5:00 PM every night of the week, at which time you can enjoy their salmon, cod, beef, chicken, pork, or duck selections. There's also a diverse appetizer menu, in addition to soups, salads, and desserts.

Next, you can spend some time at the bar, which is fully stocked with whatever you'd like to enjoy and remains open every night until about midnight.

You really can't go wrong with a meal at Five Bays Bistro, so be sure to make a reservation and stop by their Main Street location at some point.

Stop For Dessert or a Drink

After your outstanding meal in Osterville, you can check out a local ice cream shop or bar, as well.

Gone Chocolate is a popular place for dessert, featuring dozens of ice cream and frozen yogurt flavors, in addition to sundaes made with their famous homemade fudge. Other offerings include truffles, caramels, and boxed chocolates.

Or, if you're more in the mood for a liquid dessert, The Fox Hole is a dive bar that is popular with locals but is a friendly place for visitors to stop for a drink, as well. The Osterville Veteran's Association operates the bar, and you'll have to purchase a $5 membership card to get in, but the drinks are cheap, and pool and foosball tables are waiting for you. There's karaoke on weekends in the summer, too.

Your Osterville Vacation

In addition to its dinner restaurants, Osterville's Main Street is also home to Earthly Delights and 3 Wianno, both of which are popular lunch restaurants that also serve breakfast. You can also grab breakfast or lunch at The Pineapple Caper Cafe, a small eatery just off Main Street.

If you're in the mood for cooking at your vacation rental, Fancy's Market is a butcher, produce market, bakery, and beer & wine store in one. They also make prepared meals, if you don't have time to cook for yourself.

No matter which option you choose, you're sure to find some great meals during your time in Osterville. Your days here will surely be active, thanks to the beaches, forests, shops, and marinas, so it's nice to know that you can eat like royalty in Osterville after a busy day spent exploring the sights.


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