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Upper Valley Fall Bucket List: Orchards, Festivals & Trails

Variety of colorful pumpkins and squash on a wooden table at a Farmers Market during the Autumn Harvest season in Woodstock, Vermont.

Seasonal Outings in the Upper Valley

Fall in New England never fails to deliver. Crisp mornings, brilliant foliage, and weekends that invite us to slow down and savor the season. Whether you’re hunting for the perfect pumpkin, sipping cider, or wandering trails dressed in autumn color, the Upper Valley has no shortage of ways to celebrate.

Here are a few of our favorite stops this fall:

Patch Orchards – Lebanon, NH

Perched at the top of Churchill Way, Patch Orchards has been growing apples since 1775. Pick-your-own is open through late October, with a variety of apples ready for baskets and bushels. Afterward, stop by the Tasting Room to sample their house-made hard cider. Open daily, 10–5. For another local favorite check out our post on Whitman Orchard in Quechee.

Riverview Farm – Plainfield, NH

Pumpkins of every shape and size await at this Connecticut River farmstead. Pick your own from the patch or browse the curated rows of pre-picked pumpkins, gourds, and heirloom winter squash to carry you through the colder months. The corn maze is an annual favorite—worth the trip on its own. Open Wed–Sun, 10–5:30.

Lucky’s Coffee Garage – Lebanon, NH

Set in a renovated 3-bay garage downtown, Lucky’s blends specialty coffee, fresh-baked treats, and a welcoming community atmosphere. It’s the perfect warm-up stop after orchard wandering or leaf-peeping. Outdoor seating available as long as the season—and your sweater—allow.

Claremont Brewfest – Claremont, NH

Hosted by the Claremont Kiwanis Club, this one-day festival celebrates craft beer, community, and local flavor. With 30+ New England breweries, live music, and local food, it’s a showcase of creativity in every pour. Held at the Claremont Visitor Center, 14 North Street.

Apples & Crafts Fair + Food Truck Festival – Woodstock, VT

Now in its 51st year, this October festival is a fall tradition. Over 100 artisans, makers, and food vendors gather at Maxham Meadow Way, creating a vibrant mix of Vermont craftsmanship and culinary treats. October 11 & 12, 10–4.

Linny Levin Trail & Zebedee Wetlands – Thetford, VT

For a quieter fall outing, head to the Linny Levin Trail in Thetford. This community-conserved wetland, complete with beaver-maintained ponds, offers a peaceful walk with plenty of vantage points for foliage and wildlife watching. For more of our favorite local hikes check out our post 5 Breathtaking Views in the Upper Valley.

Fall is fleeting in the Upper Valley, but it’s also unforgettable. Whether you’re carving pumpkins, sipping cider, or simply walking a trail under golden leaves, we hope these stops add a little inspiration to your own seasonal bucket list.

Richard Higgerson