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A Perfect Long Weekend Holiday Itinerary in Southwestern Vermont

Spend your holiday weekend in Southwestern Vermont, where the mountains meet charming villages filled with unique shops, cozy restaurants, and winter fun. From skiing down Stratton Mountain’s powdery slopes to discovering one-of-a-kind gifts in eclectic shops, here's a guide to an unforgettable weekend in The Shires!

The Shires of Southwestern Vermont:

A picturesque New England region nestled in the Southwesternmost corner of Vermont, the geographic designation may be Bennington County but in recent years residents and visitors alike have come to affectionately call this area, The Shires of Southwestern Vermont.

This beautiful region between the Taconic and Green Mountains has the unusual distinction of having two “shire” towns, traditionally referred to as county seats. Anchored by Bennington, the South Shire, and Manchester, the North Shire, the region is a collective of 15 quintessential Vermont towns and villages connected by a scenic ribbon of highway known as Historic Route 7A (now The Shires of Vermont Byway).

Surrounded by Vermont’s famous mountain range and enriched by the many waterways including the Battenkill and Walloomsac, The Shires of Vermont is world-renowned as a four-season destination for those seeking the authentic Vermont experience. Equally attractive to both residents and visitors of the area is the relative closeness to major metropolitan areas including New York City, Hartford, Boston, Northern New Jersey, the Berkshires and Canada.

Already united by a common sense of place, history and culture, the region also possesses abundant recreational resources, a proud agricultural heritage and a robust entrepreneurial spirit. A wide range of culinary, lodging and shopping experiences await curious travelers along our highways, byways, country roads, on mountainsides and busy Main Streets.

The people of The Shires of Southwestern Vermont look forward to welcoming you to this place we call home.

But, what is a Shire?

A Shire Town is county seat. Vermont has 14 counties – each has one seat, except the Shire Towns of southwestern Vermont where there is a South Shire – Bennington and a North Shire – Manchester.

The word “shire” derives from the Old English sćir, from the Proto-Germanic *skizo (Old High German: sćira), denoting an 'official charge' a 'district under a governor', and a 'care'.

The shire in early days was governed by an ealdorman and in the later Anglo-Saxon period by a royal official known as a "shire reeve" or sheriff.