As the cold weather begins to creep into The Shires and twinkling lights brighten our villages, there’s no better time to settle in with a craft cocktail and good company. Whether you’re near Bennington or Manchester, The Shires of Southwestern Vermont offer no shortage of cozy corners, warm fireplaces, and creative bartenders ready to help you toast the season.

1. Union South Pub & Provisions — Downtown Bennington

Inside the beautifully restored Putnam Block, Union South is a welcoming mix of modern style and local spirit. The bar features polished wood, soft lighting, and a well-curated cocktail menu that changes with the seasons.
Must-try: Their smoked maple old fashioned or the winter-spiced sangria.
Warm perks: Cozy booths, friendly bartenders, and a bustling yet relaxed downtown vibe.

2. Mt. Anthony Country Club – The Grille — Bennington

The public restaurant and bar at Mt. Anthony Country Club is open year-round and offers a panoramic view of the Green Mountains. After a chilly day outside, head to the Grille for a fireside seat and a craft drink.
Must-try: Vermont bourbon mule or their classic martini.
Warm perks: Fireplace seating, friendly regulars, and big windows overlooking the winter golf course landscape and Bennington Battle Monument.

3. Copper Grouse — Manchester Village

Housed inside the elegant Kimpton Taconic Hotel, the Copper Grouse is where rustic Vermont charm meets big-city mixology. Wood-paneled walls, a roaring stone fireplace, and leather seating make it the ultimate après-ski stop.
Must-try: The signature Copper Grouse Manhattan featuring Vermont maple bitters.
Warm perks: Massive stone fireplace, local spirits, and bartenders who can craft both classics and creative twists.

4. Johnny Seesaws — Peru

A true Vermont legend. Since the 1930s, Johnny Seesaws has been serving travelers and locals from its ski-lodge perch near Bromley Mountain. Today, the beautifully restored lodge features The Dining Room and The Tavern, both buzzing with après-ski energy.
Must-try: Hot toddy or mulled cider with a splash of local bourbon.
Warm perks: Stone fireplace, reclaimed-wood bar, and an unmistakable mountain-lodge atmosphere perfect for cozy winter nights.

5. The Miller’s Toll Dinner Club & Lounge — Bennington

A chic yet comfortable lounge known for its hand-crafted cocktails and ambient lighting. The Miller’s Toll channels vintage speakeasy charm while staying thoroughly Vermont.
Must-try: Espresso martini or their barrel-aged negroni.
Warm perks: Candlelight glow, elegant bar seating, and a perfect date-night atmosphere.

6. 421 Craft Bar & Kitchen — Bennington

This Main Street hotspot combines great cocktails, hearty food, and a social bar vibe. It’s where locals meet after work or visitors unwind after exploring the Bennington Museum or downtown shops.
Must-try: Their rotating craft-cocktail list or the smoked whiskey sour.
Warm perks: Brick oven warmth, friendly staff, and a lively but laid-back bar scene.

7. Barrows House Restaurant & Tavern — Dorset

Part of the renowned Dorset Inn family, Barrows House is pure storybook Vermont — white clapboard inn, colonial charm, and a cozy tavern where locals and travelers gather. The wood-burning fireplace and candlelit tables make it an ideal winter hideaway.
Must-try: The Dorset maple bourbon smash or the mulled wine.
Warm perks: Crackling fireplace, colonial tavern bar, warm hospitality, and an intimate setting.

🎄 Final Thoughts

From the candlelit corners of Bennington’s lounges to the mountain-lodge bars of Manchester and Peru, winter in The Shires invites you to slow down, warm up, and savor the season. Whether you’re clinking glasses fireside or sampling local spirits, these destinations embody the heart of Vermont hospitality.

So bundle up, grab your friends, and explore these seven cozy cocktail havens — because warmth in The Shires is best served with good spirits.