From Manchester-Boston Regional Airport, collect your rental car and take NH-101 west, then NH-12 south to Fitzwilliam—roughly 1¼–1½ hours behind the wheel, plus time for the rental counter and traffic. Once in the village, park near Fitzwilliam Common and stretch your legs with a 30–45-minute loop past the historic meetinghouse; it’s an easy, pleasant introduction to the town. Then drive east to Rhododendron State Park for a quiet woodland walk. In early October, look for fall color among the evergreens and maples; allow about an hour, wear shoes suited to uneven trails, and check the park’s current access and any day-use fee before you go.
Continue south to Cathedral of the Pines in Rindge, about a 20-minute drive from the park. Give yourself around an hour for the hilltop grounds and outdoor memorial, but check its visitor information before setting out—hours and access can vary by season and weather. Finish in Peterborough at Harlow’s Pub, roughly 15 minutes away, for a relaxed dinner and, if scheduled, live music. Budget about $20–35 per person; because it’s Monday, confirm the pub’s hours and music lineup before you leave Rindge.
Leave Fitzwilliam early enough to reach Stowe in the morning; the drive is a substantial part of the day, and the Stowe and Waterbury stops add time. At the Stowe Recreation Path, spend about 1–1½ hours walking or biking beside the river, with mountain views when the weather cooperates. The path has multiple access points, so check trail and bike-rental details locally before setting out; a short out-and-back is an easy way to keep the day flexible.
Drive about 20 minutes to Cold Hollow Cider Mill in Waterbury Center for 45–60 minutes of cider sampling and browsing Vermont-made foods. It’s a popular stop, so expect company; check current hours before you go, and don’t count on every tasting being available late in the day. Continue to Church Street Marketplace in Burlington—roughly 30 minutes by car—and allow 1–1½ hours to wander the pedestrian-friendly blocks, shop, or grab a coffee. Street and garage parking are available nearby; budget a little time to find a spot.
Plan dinner at Hen of the Wood for seasonal Vermont cooking; allow around 1½ hours and roughly $40–70 per person before drinks and tip, and reserve ahead. Important: the Burlington location has been reported closed, so confirm it is operating for your dates before building the evening around it. To keep your final stop near sunset, aim for an early dinner, then head to the Burlington waterfront for a 45-minute lakeside walk; early October sunset is around 6:15 p.m., so check the exact time that day. If dinner runs later, the shoreline is still a lovely place to finish, though it may be dark.
Leave Burlington early; the drive to Jeffersonville via I-89 and VT-15 takes about 45–55 minutes, and you’ll want to be on Route 108 in the morning for the best light and less traffic. Check Vermont’s road-status updates before setting out: Smugglers’ Notch can close seasonally, and the pass is narrow, winding, and not a place to rush. Allow 1–1½ hours for the scenic drive between Jeffersonville and Stowe, including brief viewpoint stops, then return toward the notch for Smugglers’ Notch State Park. Give yourself 45–60 minutes for a short walk among the boulders; parking is limited, so use signed pull-offs and don’t stop where you block the road.
Back in Jeffersonville, take about 45 minutes to browse the compact village shops and pause for coffee—hours can vary on a weekday, so check what’s open as you arrive. Then settle in for an early lunch at 158 Main Restaurant & Bakery, a relaxed spot for Vermont comfort food; budget roughly $15–30 per person and check current kitchen hours before you go.
After lunch, head south for Manchester-Boston Regional Airport via Stowe and Waterbury to I-89, then I-93. Plan on roughly 3½–4 hours of driving, plus time for fuel, traffic, and rental-car return. Leaving Jeffersonville in the early afternoon keeps the airport run more comfortable; confirm your flight’s rental-return deadline and aim to arrive with a generous buffer.
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