Frommer'sFrommer's
    12 Activities

    Southern Vermont Vistas: A Scenic Round Trip From Boston

    Southern Vermont Vistas: A Scenic Round Trip From Boston
    Starts from

    Boston

    Transportation

    By Car

    Guidance

    Self-Guided

    Activities

    12

    Duration

    2 days

    Length

    217 mi

    Guide details

    Starts from

    Boston

    Transportation

    By Car

    Guidance

    Self-Guided

    Duration

    2 days

    Length

    217 mi

    • Natural Attractions
    • Adventure
    Map preview
    Kelsey Perrett

    Kelsey Perrett

    Travel Expert

    • Have your camera ready for stunning photographs of Vermont farmland.
    • Enjoy panoramic views from great heights at Hogback Mountain and the Bennington Battle Monument.
    • Dive deep into the rich natural history of the region.
    Translated by
    Southern Vermont is characterized by its rolling Green Mountains and laid-back towns set against dramatic scenery. Travel through the Brattleboro, Bennington, and Woodstock regions on this relaxing two-day trip. Immerse yourself in the rustic life of local farmers, learn more about the natural history of the region, and see various scenic landscapes of Vermont.
    This road trip can be done any time of year, but to have a full-fledged experience of the activities, the better period is from April to October.
    Translated by

    Categories

    • Natural Attractions
    • Adventure
    Southern Vermont is characterized by its rolling Green Mountains and laid-back towns set against dramatic scenery. Travel through the Brattleboro, Bennington, and Woodstock regions on this relaxing two-day trip. Immerse yourself in the rustic life of local farmers, learn more about the natural history of the region, and see various scenic landscapes of Vermont.
    This road trip can be done any time of year, but to have a full-fledged experience of the activities, the better period is from April to October.
    Translated by
    Kelsey Perrett

    Kelsey Perrett

    Travel Expert

    • Have your camera ready for stunning photographs of Vermont farmland.
    • Enjoy panoramic views from great heights at Hogback Mountain and the Bennington Battle Monument.
    • Dive deep into the rich natural history of the region.
    Translated by

    Travel itinerary

    Boston to Bennington: A Journey Through Farms and Fields
    6 Activities

    Day 1

    45 mi

    Boston to Bennington: A Journey Through Farms and Fields

    On the first day of the trip, you’ll head west from Boston, Massachusetts. After exploring the eclectic downtown of Brattleboro, Vermont, you'll take the Molly Stark Scenic Byway over the gap of Hogback Mountain, leading you to Bennington, Vermont.
    Boston Bound: From Galleries to Green Fields
    6 Activities

    Day 2

    172 mi

    Boston Bound: From Galleries to Green Fields

    Wake up and drive north to the town of Manchester, Vermont. After exploring the local art, you’ll travel along the Ottauquechee River to historic Woodstock, Vermont, and see various nature views and quaint farms.
    Map preview
    Frommer's

    Timescenery Ltd, C/O Redfern Legal Llp, 7 Henrietta Street,
    Covent Garden, London, WC2E 8PS, United Kingdom.

    +44 (0) 800 041 8483
    [email protected]

    © 2025 Timescenery Ltd. All rights reserved.