My 5 Day New England Fall Road Trip Itinerary

For as long as I can remember, I’ve dreamed of experiencing fall in New England. Growing up in Texas, “fall” mostly meant slightly cooler air and maybe wearing a light jacket by November. Real fall—with its vibrant foliage, crisp apple-picking weather, and charming small towns—felt like a fairytale. So, when my sisters and I decided to plan a five-day New England road trip, I was over the moon.

What unfolded was a whirlwind adventure through Massachusetts, Vermont, New Hampshire, Maine, and Rhode Island.

Every minute was accounted for, and while there are a few things I’d tweak for next time, it was the perfect introduction to New England’s autumn.

Months of meticulous planning culminated in this unforgettable 5 day New England road trip itinerary I’m delighted to share with you.

Along the way, I’ll offer insights on my favorite stops, lessons learned, and the places worth revisiting or skipping altogether.

Day 1: Getting to New England

We flew into Boston Logan International a day before our road trip and stayed in an airport hotel so we could wake early the following day and pick up our rental car.

We purchased Hop-On and Hop-Off bus tickets to see the best of Boston since we weren’t picking up our car until the morning.

Day 2: Boston to Stowe, Vermont

Being well rested, we picked up our rental car and left Boston early, heading northwest to Stowe, Vermont.

The road trip from Boston to Stowe includes stops in quintessential New England towns, like Woodstock, to see the iconic Sleepy Hollow Farm, covered bridges, and scenic landscape.

Highlights for Day 2:

• Woodstock, VT: This Hallmark-like town needs more time. I would definitely stay the night here if time allowed.
• Ben & Jerry’s Factory: Just outside Stowe in Waterbury, this was a fun and delicious stop. Don’t skip the flavor graveyard!
• Smugglers’ Notch Scenic Drive: The winding roads offered incredible views of the mountains and forests. We stopped frequently for photos.
• Downtown Stowe: We strolled along the main street, popping into cozy shops and indulging in maple-flavored treats.

Hotels in Stowe: I recommend the Green Mountain Inn, a charming inn with a fireplace in the lobby and warm, welcoming vibes. For something more luxurious, check out Topnotch Resort.

Tip: Stowe deserves more time. I’d recommend staying two nights if your schedule allows.

Visit the LL Bean Flagship Store

On our road trip, we wanted to visit the LL Bean Flagship Store in Freeport, Maine.

The LL Bean Flagship store is an iconic destination for outdoor enthusiasts and shoppers alike.

Spanning over 200,000 square feet, it’s a retail paradise with everything from high-quality outdoor gear to cozy apparel.

What sets this store apart is the fact that it never closes.

The flagship store is open 24/7, 365 days a year, allowing visitors to shop whenever the mood strikes.

Beyond shopping, the store also hosts events and offers a wide range of outdoor activities, making it a must-visit destination in the heart of Maine.

Go Apple Picking

While driving through New Hampshire, plan a visit to Applecrest Farm Orchards in Hampton Falls to visit a fantastic apple-picking farm.

Applecrest Farm Orchards is the oldest and largest orchard in New Hampshire, with acres and acres of fruit trees and fields of flowers.

It is so big that you even take a tractor out to pick your fruit or flowers.

Honestly, these are the best apples I have ever tasted. Hands down!

Try the Lobster Macaroni and Cheese at The Orchard Grille at Applecrest Farm. It is delicious

Day 4: Escape to the Coast of Maine

After a full day in the car on day three, we spent day four exploring the coastal towns of Maine.

Although you may not see much foliage along the coast in the early fall, Ogunquit and Kennebunkport are two beachfront cities you won’t want to miss on your five day New England fall road trip.

The Maine coast is a showstopper.

We explored Ogunquit, walked the Marginal Way (a scenic coastal path), and headed to Kennebunkport, a picturesque town that felt like a movie set.

You won’t find many people visiting during the fall, so it will seem like you have the coast to yourself.

Along the Coast to Cape Cod

After spending the morning in Ogunquit and Kennebunkport while en route to Cape Cod, we made a quick stop in Salem, known for its historic Salem Witch Trials.

What we thought would be a quick, fun visit around Halloween time, turned into lots of crowds and sitting in traffic.

I would skip a visit to Salem, and head straight to Cape Cod.

You will want more time after you fall in love with the beaches of Cape Cod.

Highlights of Day 4:

• Marginal Way: This 1.25-mile path along the rocky coast of Ogunquit offers spectacular ocean views.
• Kennebunkport: We loved Dock Square’s shops and had a fabulous lobster roll at The Clam Shack.
• Walker’s Point: The Bush Compound is a short drive outside of Kennebunkport. Being from Texas, we had to see it.

Hotel: That evening, we drove south to Cape Cod and stayed at the Eagle Wing Inn. It’s a lovely roadside inn, and the hospitality is impeccable.

Tip: Many coastal attractions close for the season after Columbus Day, so plan accordingly.

Day 5: Cape Cod and Home

On our last day, we drove to the northern tip of Cape Cod in Provincetown to have breakfast and enjoy the sunrise over the beach.

Then, we packed up to drive to Rhode Island for a flight home.

Highlights:

• Cape Cod National Seashore: Even in late fall, the beaches were breathtaking. We visited Nauset Light Beach and marveled at the dunes.
• Provincetown, MA: We had to visit this adorable seaside town to see the site of the Mayflower’s landing!

Tips for Your 5 Day New England Road Trip

We logged over 1,000 miles in five short days, and it was totally worth the adventure. Now, if I could afford three weeks on the East Coast, I would, without a doubt, explore much more. But, if you only have five days, you will still have a fantastic time.

If I had to change the itinerary after visiting, here is what I would do differently.

• I would spend more time in Vermont, especially in the Stowe area.
• The L.L. Bean flagship store is neat, but I would skip it and spend more time on the coast of Maine. I regret missing out on going to Bar Harbor and Acadia National Park.
• The Kancamagus Highway is 100% worth the drive.
• Cape Cod is amazing, but I would save it for its own trip. The time it took to drive there is not worth it since many restaurants and shops are closed for the season.
• Timing is everything! Peak foliage varies by region. Late September to mid-October is ideal, but there is no way to predict what changes you will see truly.

This whirlwind five-day road trip across five New England states in the fall was everything I hoped for.

Our non-stop vacation was a thrilling adventure that left us breathless and utterly content.

The memories we created, the sights we witnessed, and the experiences we made were worth every mile.

While this adventure is achievable, I wouldn’t describe it as a leisurely getaway. Expect to be constantly on the move.

In conclusion, no matter which route you take, New England is beautiful in the fall.

If you’ve been dreaming of a fall road trip through New England, now’s the time to start planning. You won’t regret it.