After your 1:15 p.m. arrival, collect the rental car and head north on I-93 to Concord; from there, the route to Contoocook is a short detour before you continue west and north toward I-89, VT-107, and VT-100 for Killington. The direct drive to Green Trails Inn is about 2½–3 hours without stops; with the lunch and bridge visit, plan on roughly 4–5 hours after leaving the airport, depending on rental-car lines and foliage traffic. The Works Café is a good relaxed stop for sandwiches, salads, and café fare (around $15–25 per person), but Sunday hours may be limited, so check its closing time before you fly; if your arrival runs late, call ahead to make sure you can still eat there.
From Concord, allow about 20–25 minutes to reach Contoocook Railroad Depot and Covered Bridge. The depot and nearby bridge make a pleasant, brief visit, with mostly level walking; allow 30–45 minutes, and take care around the road and bridge approaches. Then continue toward Killington via I-89 and VT-107/VT-100. Check in at Green Trails Inn and keep the evening easy—you’ll have had a long travel day, and daylight fades earlier in October.
Plan to reach Grafton Village Cheese Company around 11:30 a.m.; give yourselves about 45 minutes to browse and sample. Then it’s a short drive or easy walk through the compact village to Grafton Village Store for a casual lunch—allow about an hour and budget roughly $15–25 per person. Check the store’s hours before you leave, as small-town schedules can vary by day.
After lunch, visit Grafton Covered Bridge for a quick roadside look and photos; you won’t need to tackle a long walk. Continue to The Nature Museum for an unhurried hour with its natural-history exhibits. Its seasonal schedule can be limited, so call or check its current hours before setting out—especially for a Monday visit—and leave a little flexibility in case it opens later than expected.
Finish at The Grafton Inn, where you can settle in for a drink or early dinner in the historic surroundings. Dinner is roughly $25–45 per person; check the restaurant’s Monday service hours and consider calling ahead if you’d like a table. The village is small, so there’s no need to rush between stops—just allow extra time for foliage-season traffic on the drive.
Start at Quechee Gorge, where you can take in the “Little Grand Canyon of Vermont” from the bridge and roadside viewpoint without tackling the steep trail. Allow 30–45 minutes; the bridge viewpoint is close to parking, though the area can be busy in foliage season. Then head to Simon Pearce for lunch, a short drive away. Reserve a table if you can—plan on about $25–45 per person—and ask when glassblowing demonstrations are running, since the schedule can vary. The viewing area and shop make a nice unhurried stop even if the glassblowers aren’t working when you arrive.
Continue to Billings Farm & Museum in Woodstock and give yourselves 1½–2 hours for the farm exhibits and animals. In early October it is typically open daily, but check the museum’s current hours before setting out; admission is generally around $20 per adult, with possible senior pricing. Stick to the flatter paths and take breaks as needed. Afterward, drive into the village and visit Middle Covered Bridge for a short, level stroll and photos—about 20 minutes is plenty.
Finish with dinner at the Woodstock Inn & Resort, right in the village. Expect roughly $35–60 per person before drinks and tip; reservations are wise during peak foliage weeks. It’s a relaxed place to settle in after a full day, and you can enjoy a little window-shopping or a gentle wander around the village green if you have energy.
Take a relaxed scenic loop around Pico Mountain and the Killington resort area, allowing about 45 minutes for mountain scenery and photo stops. You can enjoy the views from the roads and pull-offs without taking a hike; don’t count on driving all the way to a summit, since resort roads and facilities may be restricted or seasonal. Fall foliage brings slow traffic, so leave a little slack before lunch.
Continue north to Pittsfield Village for lunch at Clear River Tavern, a casual local stop on Vermont Route 100; budget roughly $15–30 per person and check that day’s hours before setting out, as small-town schedules can shift in autumn. After lunch, stay on Route 100 north to Moss Glen Falls in Granville. The falls are visible near the roadside pull-off, making this a brief stop of about 20–30 minutes; parking is limited, and the trail beyond the viewing area can be rough, so there’s no need to venture farther.
Drive north to Warren Village for about an hour to browse its small shops and take in the historic village center. Then continue to Warren Falls for 20–30 minutes of river scenery. A note for your footing: the popular pools are reached by rocky, uneven paths, so they aren’t a good fit if you’re avoiding uneven terrain; enjoy the river only from a safe roadside vantage point if one is available, and skip the stop rather than attempting the access trail. Check the forecast and road conditions before heading out, since fall showers can make rocks and paths slippery.
Leave Killington around 6:30–7 a.m. for the long drive to North Conway via VT-100 and NH-112, including the Kancamagus Highway. Allow roughly 3½–4 hours behind the wheel before sightseeing, and more in peak foliage traffic; use signed pullouts only, since stopping on the road is unsafe. Pack breakfast and water, and check the weather and road conditions before setting out.
At Lower Falls, give yourselves 30–45 minutes to enjoy the Swift River from the developed roadside area. Paths may still be uneven, so take your time and stay within your comfort level. Continue to Sabbaday Falls only if the approach feels manageable: it has uneven footing and steps, and is not a good fit if those are uncomfortable. Allow about 45 minutes if you go, but skipping it is the sensible choice if you want to protect time and energy for the train.
Check the day’s departure times for the roughly one-hour round-trip excursion on the Conway Scenic Railroad before you leave; October foliage season can be busy, so reserve ahead if possible. The train does not go to Littleton. After the ride, drive via NH-302 toward Twin Mountain and US-3 to the Eastgate Inn—allow about 1½–2 hours, then check in and find dinner nearby. This is a full day, so if the train schedule won’t fit comfortably, skip Sabbaday Falls rather than rushing the drive or your rail stop.
After the drive from Littleton, start at Cold Hollow Cider Mill in Waterbury Center. Give yourselves about an hour to browse and sample cider treats; the mill and shop are generally open daily, but check the current hours before setting out. It’s a popular foliage-season stop, so an earlier arrival usually means easier parking and a less crowded shop.
Continue to The Bench in Stowe for a relaxed lunch—wood-fired pizza and comfort food, typically around $20–35 per person. Afterward, head to the Stowe Recreation Path and choose a short, level stretch for 45–60 minutes of river and mountain views. You don’t need to walk the whole path; turn back whenever you’ve had enough, and check the path’s access and parking options before choosing your starting point.
Drive back toward Waterbury for Ben & Jerry’s Waterbury Factory. Allow about an hour for the shop and grounds; factory-tour availability and hours can change, so check ahead and reserve if tours are offered. Then return to Stowe for Von Trapp Bierhall, where you can meet your friends over Austrian-inspired fare in a scenic mountain setting. Budget roughly $25–45 per person; a reservation is sensible on a busy fall Friday.
For the direct run from Stowe to Manchester-Boston Regional Airport, allow 2½–3 hours via VT-100 south, I-89 south, and I-93 south, plus time for foliage traffic, fuel, and rental-car return. Aim to reach the airport at least two hours before your flight. If your flight is late enough for breakfast, Littleton Diner is a good classic-diner stop—but it lies north of the direct route, so going there via US-2 adds substantial driving time. Budget roughly $15–25 per person, and check the diner’s current hours before setting out.
If you make the Littleton Diner detour, continue south toward Concord and use it as a flexible 30–45-minute break for coffee, a stretch, or fuel; cafés and gas stations are convenient to the highway. Otherwise, stay on the direct route and stop in Concord only if you need a rest. From there, continue to Manchester-Boston Regional Airport for the rental-car return and your flight.
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