There’s a moment every year when Hampshire County exhales.
Lights blink on downtown, wreaths appear on front doors, and the hills start to glow like they’re in on the secret. It’s subtle at first, then suddenly the whole place feels wrapped in its own quiet sparkle. The Hampshire Highlands Holiday Guide brings all of that magic together.
That’s the season we’re stepping into now.
And this year’s Holiday Guide pulls every bit of that charm into one place.
What’s Inside the Hampshire Highlands Holiday Guide
This year’s Month of Merriment is packed from Thanksgiving Eve through Christmas. The guide gathers everything happening across the county — big moments, small joys, and all the little traditions that make the season feel warm and familiar.
You’ll find:
• Thanksgiving Eve Carriage Rides in historic Romney
• The Cookie Crawl and Tree Lighting
• Festival of Trees opening night
• Christkindl Market at Taggart Hall
• McDaniel Farms’ Christmas on the Farm
• Artisan markets at The River House
• Workshops, wreath making, tastings, open houses, and more
• Local shops and boutiques decked out for the season
• Dining, cozy stays, winter experiences, and hidden gems spread across the Highlands
It’s a season-long invitation to wander, savor, and take your time with the places that make this region feel special.
The Feel of the Highlands in Winter
Winter in the Hampshire Highlands has its own rhythm — clear mornings, frosty fields, and families packing into local shops with bags of baked goods and handmade gifts. You’ll spot children in holiday dresses on the North Pole Express. You’ll find neighbors holding cocoa at the parade. You’ll hear old buildings come alive with music and workshops that feel like stepping into a simpler time.
The guide captures all of that:
the sparkle, the nostalgia, the sense that you don’t have to rush here.
The People and Places You’ll Meet
This season brings out some of the best of the county.
• Anderson’s Corner, shimmering with gifts, tastings, and their legendary Men’s Night
• 1762 Wine & Brew and The White House on Main hosting cozy nights, carriage rides, and tastings
• Slanesville General Store, where Christmas feels personal and Clyde the Basset Hound is basically staff
• Farmhouse Studio, Nellie’s Flower Farm, New Leaf, and our farm markets, each adding their own holiday magic
• Potomac Eagle, offering both joyful North Pole fun and peaceful winter canyon rides
• Local restaurants serving comfort food you remember years later
• Boutiques and makers who put heart and craft into every holiday item
It’s the kind of lineup you only get in a place that cares about community. In the Hampshire Highlands Holiday Guide, you’ll find events, cozy shops, winter stays, and festive markets across the county.
Plan Your Season
Whether you’re planning a weekend visit or you live right down the road, the Holiday Guide makes it easy to build your own month of merriment. Carriage rides, gift shopping, wreath workshops, cozy cafés, farm stops, gingerbread moments, and everything in between — all mapped out for you.
Explore the full guide here: https://simplebooklet.com/hampshirehighlandsholidayguide2025
Here’s to warm lights, crisp air, handmade treasures, and a holiday season that feels beautifully local — and beautifully yours.
Looking for places to stay? Explore our lodging options: https://hampshirehighlands.com/rest-your-head/
