Pizza Stone VT (291 Pleasant St, Chester, VT 05143)
MacLaomainn’s Scottish Pub (52 S Main St, Chester, VT 05143)
Country Girl Diner (46 VT-103, Chester, VT 05143)
Ye Olde Bradford Tavern (40 The Common, Chester, VT 05143)
Southern Pie Cafe (94 The Common, Chester, VT 05143)
Heritage Deli and Bakery (642 VT-103, Chester, VT 05143)
Maria’s Mexican Food (571 VT-103, Chester, VT 05143)
The Copper Fox (56 Main St #1, Springfield, VT 05156)
Endless Creations Pottery Studio (23 Maple St, Chester, VT, 05143): Walk-in pottery painting — head in and paint your piece, the studio will kiln fire it, and you can either pick it up or have it shipped to you!
Stone House Antique Center (557 Vermont Route 103 S, Chester, VT 05143): Featuring antiques and collectibles, shop around the antique center’s 90+ vendors!
Rose Arbour (55 School St. Chester, VT 05143): A tearoom, bed and breakfast and gift shop in Chester, Vermont.
Sage Jewelry and Gifts (78 The Common, Chester, VT 05143): Gift shop featuring jewelry and other American and fair trade crafted gifts
There are two hiking trails in Chester, VT. You can find information on how to access each of the trailheads on the Chester town website.
Lost Mine Trail (2.2 mile loop)
Butternut Hill Trail (1.9 mile loop)
Mount Ascutney State Park: Mount Ascutney has some lovely hiking trails — or you can drive to the top and see the summit via car if you so choose! Kylie and Caleb (plus Sam Harris) have hiked Ascutney twice and only successfully reached the summit once (though this was due to a late start, not any particular trail difficulty).
Healdville Trail (6.0 mile up and down): The Healdville Trail climbs from the base to the summit of Okemo Mountain in Ludlow and Mount Holly. Highlights of this trail include the former fire lookout tower on the summit and a vista along the trail with views to the north and west.
Buttermilk Falls (Ludlow, VT): Buttermilk Falls is a series of waterfalls and swimming holes in Ludlow.
Covered Bridges: Vermont has many covered bridges — and you can visit a few while in southern Vermont! Check out the guide to find some local covered bridges to visit and explore. Some of them will even take you to New Hampshire, home of Jed Bartlet.
Leaf Peeping: It’s that time of year, folks. Go see the fall foliage! Live your best autumnal aesthetic life!
Harpoon Brewery Taproom and Beer Garden (336 Ruth Carney Drive, Windsor, VT 05089)
WhistlePig Whiskey Parlour (1792 Quechee Main St Second Floor, White River Junction, VT 05001)
Vermont Spirits (5573 Woodstock Rd, Quechee, VT 05001)