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    Sweet Williams

    5.0 (2 reviews)

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    4 years ago

    Helpful 2
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    2 years ago

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    Grassland

    Grassland

    5.0(2 reviews)
    7.2 mi

    Grassland Dessert Cafe is more than just an ice cream shop -- it's Lakeville's new heartbeat…read more Owners Bill and Lorna have lovingly brought back to life the old Lakeville pharmacy, transforming it into a vibrant, joyful gathering spot that captures the spirit of small-town magic with every scoop. Step inside and you're greeted by the warm smile of proprietor Bill Colgan, whose boyhood memories of the Skipper Dipper on Long Island inspired this delightful adventure. He's recreated that nostalgic charm here -- with a twist! Craving a classic? The Orange Freeze and Root Beer Float will send you straight back to summer afternoons gone by. Want something modern? Don't miss flavors from Gifford's Ice Cream, like the rich, espresso-swirled Campfire S'mores, or the wildly indulgent Sea Salt Caramel Cookie Crunch -- the kind of flavors you can't stop thinking about. And if you're celebrating -- or just feel like going BIG -- order the Everything But the Garage Sink: a jaw-dropping creation with 20 scoops of ice cream, piled high with toppings. It's perfect for birthdays, school advisory groups, or a spontaneous family feast. This isn't just a dessert stop -- it's a place where memories are made. Whether you're a local or passing through the Northwest Corner, Grassland Dessert Cafe is a must-visit. Grab a cone, say hi to Bill, and feel the joy of community, one sweet bite at a time.m

    Such a fantastic addition to our community! The ice cream, shakes, açaí bowls, and more are all…read moretop-notch, and the iced strawberry matcha is a total standout--don't miss it. Warm, friendly service and inviting seating both indoors and out make this a spot you'll want to return to. Huge kudos to the team on a job well done!

    Photos
    Grassland - Grassland decorated for July 4th!

    Grassland decorated for July 4th!

    Grassland - Greek Yogurt Bowl

    Greek Yogurt Bowl

    Grassland

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    Off The Trail Cafe

    Off The Trail Cafe

    4.3(3 reviews)
    5.2 mi

    ORIGIN: After much anticipation, Liz and Howie Ives opened…read moreOff the Trail Cafe at the beginning of summer 2025. The name of the cafe is a reference to the proximity of the Appalachian Trail. LOCATION: The cafe is located near the town park at the beginning of charming Main Street. It is close to the Appalachian Trail, so the cafe is an especially welcoming destination for hikers. CONCEPT: Off the Trail Cafe is a place where community members, as well as visitors from afar, are welcomed to refresh, connect, and relax. EXPERIENCE: The cafe is open every day except Wednesday until 3 PM. The menu is evolving, but what is apparent is a commitment to support and showcase other businesses in the region. For example, Litchfield-based Peaches N' Cream ice cream and Millerton's Harney & Sons teas are served, and on Saturday mornings you'll find fresh donuts from North Canaan-based Pastries by Hanna in the pastry case. (Hopefully-- they don't last long!) AMBIANCE: The setting is relaxed, welcoming of all, with no pressure to leave. SERVICE: Items are ordered at the counter. TIP: The inclusion of a children's play area also highlights a value for making everybody feel welcomed to spend time in the cafe.

    The new owners took this place over last summer. They changed a few things and it looks and feels a…read morelot more welcoming. The staff is very friendly and always greets you up arrival. They have lots of indoor and outdoor seating along with lots of parking. The menu has a wide variety for both breakfast and lunch. They also offer monthly specials. Every time I go there the parking lot is full!! It's located in the center of town. Whether you are looking for something hot or cold or to sit down or get take out, off the trail has it all!

    Photos
    Off The Trail Cafe
    Off The Trail Cafe
    Off The Trail Cafe

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    Sweet Williams - desserts - Updated August 2026

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