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    Moving to Osterville, MA: Tips and Guides

    West Bay in Osterville, Massachusetts is a favorite mooring spot on the south side of Cape Cod due to its easy access to the open ocean.

    Osterville never ceases to amaze me. I always see it as the quintessential Cape Cod lifestyle, which is what makes it such a fantastic getaway and an even more amazing place to live. If you’re lucky enough to be moving to Osterville, be prepared to have the time of your life. There are just so many things to see and do. I drew up this list to help you get started.


    The entire family will love Dowses Beach. There’s a dock that’s great for fishing, and is the perfect spot for diving or simply taking in the stunning view. The rock jetties teem with fish all year ’round, and there’s plenty of bait in the area. Parking is a breeze for residents with beach stickers.

    Joshua’s Pond is another family favorite. Located off Tower Hill Road, it’s a small beach that’s somewhat hard to find, so you’ll get plenty of peace and quiet. The swimming area is roped off and there’s a lifeguard on duty until midAugust. The grassy hill that overlooks the pond is a great spot for sunbathing and also features a small play area for the kids.

    Boating and kayaking

    I’ve previously written about boating in Osterville, specifically to give some tips on what kind of boat would be perfect for the waters here. As I mentioned, there’s no one answer to that question because the waterways in Osterville are unique in all of Cape Cod.

    You can paddle or row your way around Sampson’s Island and Dead Neck – a MassAudubon wildlife sanctuary that can only be accessed by private boat or something as small as a paddleboard.

    The waters of West Bay, North Bay, Cotuit Bay, and the Seapuit River are best enjoyed by sailboat. And if you plan to go further offshore, powerboating would be the way to go.

    Boating and fishing charters abound in the area. There are a number of fullservice marinas, including:

    • Crosby Yacht Yard, Inc.
    • Nauticus Marina
    • Oyster Harbors Marine


    Biking is a great way to get around Osterville. There are scores of quiet roads that will take you to and from the beach, and mostly anywhere in the village, including the downtown and rural areas.

    Along the way, you get plenty of chances to enjoy the one-of-a-kind sights and sounds of the village, from the glorious beaches on Nantucket Sound to the quaint shops on Main Street. Check out our previous posts about touring the village on bike and the best bike stops around the village.


    Osterville’s charming downtown features excellent restaurants that draw diners from near and far. Whether you’re craving for classic Italian pasta, fresh seafood, or the juiciest steak, you’ll find plenty of fabulous choiceshere. Wimpy’s Seafood Café is a favorite destination– it’s a market, restaurant, and bar all in one. Crisp Flatbread has a rustic Italian countryside feel that matches its homemade Mediterranean fare. Then there’s the elegant Five Days Bistro, the ideal choice for an intimate and laid-back night out. Lastly, at Crosby Yacht Yard, there is the Chart Room, open seasonally and one of the best seafood venues on Cape Cod.

    If you’d like more information on Osterville as well as other Cape Cod towns and villages, please don’t hesitate to get in touch with me at 508.957.5500 or jack(at)jackcotton(dotted)com.

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