Best for: Scenic drives, cozy inns, covered bridges, and small-town charm — even when the fall color doesn’t fully show up.

6-Day Suggested Route

The Berkshires & US 7 ➜ Vermont Route 100 ➜ Stowe (2 nights) ➜ Kancamagus Highway ➜ Jackson, NH (2 nights)
Next stop? Coastal Maine.

This route runs through the heart of New England — classic towns, mountain views, and winding backroads. Even though this year’s foliage was the weakest locals had seen in a century, the trip was still great: beautiful scenery, good food, and plenty of charm.

Tip: If you can, give yourself extra days and stretch out the driving. The distances aren’t huge, but moving slower makes the trip much more enjoyable.

Day 1: The Berkshires & US 7

Driving north through the Berkshires along US 7 is a relaxed way to ease into the trip. We made plenty of detours — down narrow lanes, dirt roads, anywhere that looked interesting. Every turn seemed to reveal another farm or mountain view.

Highlights:

Stay: Stockbridge, MA — the Red Lion Inn, with its wide porch and historic charm, looked like the perfect overnight stop to kick things off. We didn’t stay there, but we both said we would next time.

Day 2: Vermont Route 100

Once in Vermont, take Route 100 north — it’s one of the best scenic drives anywhere, lined with country stores, rolling hills, and small towns.

Highlights:

• Weston: The Vermont Country Store — touristy but fun, and the whole village green is charming.
• Woodstock: Beautiful but very busy during peak weekends. Worth visiting another time when it’s quieter.
• Warren Store, Waren, VT: This ended up being one of our favorite stops for food. The Vermonter sandwich and Ultimate Grilled Cheese were both fantastic. Very tiny but cute town too!
• Cold Hollow Cider Mill. Lived up to the hype! We stopped three times for maple creemees (soft serve ice cream), cider, and apple cider donuts. It’s busy, but totally worth the chaos.

Stay: Riverside Hotel in Brattleboro — a great pit stop after a day on the road. It was a surprisingly luxurious stay and a comfortable base before heading north toward Stowe.

Tip: A lot of Vermont restaurants and shops close midweek (especially Wednesdays), so it’s worth double-checking hours when planning.

Days 3–4: Stowe, Vermont (2 nights)

Stowe ended up being one of our favorite stops — the perfect mix of scenic, walkable, and quintessentially Vermont. The village has everything you’d want: a white church steeple, covered bridges, boutique shops, and views that feel straight out of a painting. It’s easy to spend a few hours just strolling Main Street, browsing, and soaking it all in.

Highlights:

• Trapp Family Lodge Bierhall: A bit of a tourist stop, but the pretzel and brat were both very good. If the weather’s nice, the outdoor seating and mountain views make it worth it.
• Trapp Hill Road Drive: Keep driving past the main lodge and follow Trapp Hill Road down the mountain — hardly anyone was there, and it turned into one of our favorite short drives of the trip.
• Gondola Ride up Mount Mansfield: A nice option if you have time. The views are great, but not essential unless foliage is at or near peak.
• Stowe Cemetery: Peaceful and well-kept, with headstones honoring veterans dating back to the Revolutionary War — worth a few minutes for reflection and a sense of the town’s history.

Stay: Green Mountain Inn — we absolutely loved this hotel. A great stop and one we’d highly recommend: luxurious accommodations right in the center of town, with warm hospitality and everything within walking distance.

Tip: Make restaurant reservations a few weeks ahead, especially in fall — everything in Stowe fills up fast.

Day 5: The Kancamagus Highway

From Stowe, cross into New Hampshire and spend the afternoon on the Kancamagus Highway — 34 miles of mountain scenery through the White Mountains. Even without strong color, it’s a beautiful drive.

Highlights:

• Hancock Overlook, Sabbaday Falls, Rocky Gorge, and Sugar Hill Overlook — classic scenic stops along the route.
• Plan for at least 2½–3 hours to enjoy the drive and stops.
• End the day in Jackson, NH, a small, quiet town that makes a good home base for exploring Mount Washington.

Tip: The Kanc is especially beautiful in late-afternoon light — take your time, and don’t rush through it.

Days 6–7: Mount Washington & Jackson, NH (2 nights)

After finishing the Kancamagus Highway, we based ourselves in Jackson, New Hampshire — a small, quiet town at the edge of the White Mountains. It was a convenient home base for exploring Mount Washington and the surrounding area. Jackson has a covered bridge and a few restaurants and shops — just enough to make it comfortable without feeling crowded. The broader Mount Washington area offers scenic drives, great overlooks, and it’s close enough to reach both the Cog Railway and the historic Omni Resort without much effort.

Highlights:

• Mount Washington Cog Railway: A clear highlight of the trip. The ride climbs above the tree line with wide views, and the conductors share interesting history along the way.
• Red Fox Bar & Grill (Jackson): Relaxed spot with good food and friendly service — a nice place to unwind after a day in the mountains.
• White Mountain Puzzles Headquarters: Small shop but a fun stop if you enjoy puzzles; they carry the full collection.
• The Return of the Pumpkin People. The town decorates with the cutest craziest pumpkin decor – we loved the creativity and small town charm of it all!

Stay: Inn at Thorn Hill, The Wentworth, or Omni Mount Washington Resort — all good options if you’re staying longer or want more amenities (we can’t recommend where we stayed in Jackson).

Tip: Bring layers for the Cog Railway — it’s much colder at the summit than you’d expect, even on sunny days.

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Takeaways

• Even in a year without peak color, this is still a great drive.
• Vermont is all about the small towns, country stores, and easy stops — don’t rush through.
• Woodstock was too busy to just stop by —go early or off-peak if possible.
• Check midweek closures (many stores and shops were closed on Wednesday) and make restaurant reservations early.
• We didn’t plan any hikes, but there are plenty of short trails that would break up the driving nicely.
• If you can stretch your time, it’s worth slowing down and enjoying each stop a bit longer.
• Any year the timing of a visit with foliage is tricky but don’t stress that as its beautiful anytime of the year!

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➡️ Next Stop? Coastal New England

From the mountains to the coast — the perfect next leg. Head east to swap maple creemees for lobster rolls and mountain roads for coastal villages like Camden, Rockland, and Kennebunkport. Coastal New England Itinerary.