There’s nothing quite like experiencing autumn in New England. The vibrant foliage, crisp air, small town charm, and local eats make it one of the most magical destinations for a Fall getaway. Below is a detailed, day by day guide to our 2022 Fall roadtrip through Rhode Island, Massachusetts, Maine, and New Hampshire. While we covered a LOT of ground in 6 days, I highly recommend staying in these places longer than we did or breaking the trip up into multiple trips. We learned on this trip that we wished we would have narrowed down our spots as we did a lot of driving.
I will say, now that we have experienced Fall trips to most of the New England states I feel like I can give a bit more of an educated opinion. If you are looking to see the best Fall Foliage, you are going to want to visit Vermont and New Hampshire. The closer you get to the coast, the less Fall Foliage and bright colors you will see. That being said, some of these coastal towns are so darn charming in the Fall, they are well worth visiting too but you just have to know what you are getting into! So with that being said… here is our 2022 itinerary! You can see 2021 and 2023 here.
📍 Download the itinerary map here
Day 1 – Newport, Rhode Island
There’s no better way to kick off a New England fall getaway than by easing into coastal charm. Newport in autumn feels timeless – a mix of salty ocean air, crisp breezes, and Gilded Age glamour. Even just walking the Cliff Walk at golden hour sets the tone for the trip ahead.
- Fly into Boston or Providence and make your way to the coast.
- The Chanler at Cliff Walk – A luxury boutique hotel perched at the start of Newport’s famous Cliff Walk. This historic mansion overlooks the Atlantic and offers one of the most picturesque stays in Rhode Island. Staying here feels like stepping back in time but with every modern comfort. By far one of the nicest accommodations that I have ever stayed in!
- Fun Fact: The Chanler is one of the only hotels located directly on the Cliff Walk. Each of its 20 rooms is decorated in a different historical style, from Louis XVI to English Tudor.
- Pro Tip: Even if you don’t stay here, consider grabbing a cocktail or lunch on the terrace – the ocean views are incredible.
- Fun Fact: The Chanler is one of the only hotels located directly on the Cliff Walk. Each of its 20 rooms is decorated in a different historical style, from Louis XVI to English Tudor.
Day 2 – Newport – Massachusetts -Maine
Today is a true road trip day – a mix of small-town farm stops, coffee breaks, and the charm of a quintessential Maine harbor town. You’ll be covering a lot of ground, but every stop feels like a little seasonal postcard.
- Empire Tea & Coffee, Newport – A local coffee favorite, perfect for a caffeine boost before hitting the road.
- Wilson Farm, Lexington, MA -A family run farm and market dating back to 1884. In the Fall, it’s especially festive with pumpkins, gourds, apple cider donuts, and seasonal treats. It’s a great place to stock up on snacks for the road.
- Pro Tip: Their apple cider donuts sell out fast on weekends, so grab a half dozen to enjoy in the car.
- Pro Tip: Their apple cider donuts sell out fast on weekends, so grab a half dozen to enjoy in the car.
- Kennebunkport, Maine – A quintessential New England coastal town with charming shops, seafood restaurants, and harbor views. Known for its lobster rolls and coastal architecture, this town is a MUST stop. We’ve actually come back every year – this spot is one of our favorites.
- Our go-to spots:
- The Clam Shack (lobster rolls worth the hype!)
- Batson River Brewing & Distilling – Known for their inventive cocktails and cozy atmosphere. Their seasonal “Liquorwitch” cocktail is a local favorite in the fall.
- Coffee Roasters of the Kennebunks
- Fun Fact: Kennebunkport is the summer retreat of the Bush family — you can even spot Walker’s Point if you drive along Ocean Avenue.
- The Clam Shack (lobster rolls worth the hype!)
- Our go-to spots:
- Hurricane Restaurant, Kennebunkport – A classic Maine seafood restaurant with a menu featuring fresh caught fish, lobster, and oysters, all served with views of the Kennebunk River.
- Pro Tip: Don’t pass up the espresso martini – SO good!
- Pro Tip: Don’t pass up the espresso martini – SO good!
Day 3 – Coastal Maine & New Hampshire
Buckle up – this is one of those jam-packed New England days where every turn is photo-worthy. From charming cafés to apple orchards to mountain roads, it’s a mix of cozy, coastal, and breathtakingly scenic. If you have more time, stretch this day into two – it deserves it!
- Fiafia, Kennebunkport – This cute cafe offers the best seasonal lattes and healthy breakfast options like avocado toast and acai bowls.
- Carter Hill Orchard, Concord, NH – A picturesque orchard where you can pick your own apples against a backdrop of rolling hills covered in fall color. Their cider and baked goods are must tries.
- Pro Tip: Their cider donuts are made fresh daily – grab a warm one straight from the fryer.
- Pro Tip: Their cider donuts are made fresh daily – grab a warm one straight from the fryer.
- Kancamagus Highway, NH – Known as one of the best scenic byways in the United States, this 34.5-mile drive cuts through the White Mountain National Forest. Expect sweeping mountain views, vibrant foliage, and plenty of scenic overlooks.
- Fun Fact: Locals call it “The Kanc.” There’s no gas along the highway, so fuel up before starting the drive.
- Fun Fact: Locals call it “The Kanc.” There’s no gas along the highway, so fuel up before starting the drive.
- Rocky Gorge Scenic Area – A popular stop along the Kancamagus Highway. This short walk takes you to a series of waterfalls and pools formed by the Swift River, perfect for photos.
- Bethel, Maine – With a walkable village center full of shops, cafes, and historic inns, Bethel is a charming mountain town that blends small-town New England character with year-round adventure. It feels like you’re in Stars Hollow from Gilmore Girls!
- Le Mu Eats, Bethel, ME – A small, family run eatery known for its creative fusion of Asian and comfort food. Dishes like pulled pork banh mi and Korean BBQ tacos make this an unexpected gem in the Maine mountains.
Day 4 – Bethel, Maine
This day is slower and more scenic – the kind where you pull over just because the light hits the leaves perfectly. Covered bridges, breweries, waterfalls, and mountain overlooks make it feel like the most “storybook” day of the trip.
- Sunday River Bridge, Newry, ME – Also called the Artist’s Covered Bridge, this historic 1872 wooden bridge is one of the most photographed spots in Maine during peak foliage.
- Fun Fact: The bridge gets its nickname from the many painters and photographers who have captured it over the years.
- Fun Fact: The bridge gets its nickname from the many painters and photographers who have captured it over the years.
- Sunday River Brewing Company – A casual spot to enjoy local craft beers and hearty pub food after exploring the mountain area.
- Rumford Falls, Rumford, ME – One of the largest waterfalls east of the Mississippi, cascading dramatically in the middle of a small town. In autumn, the colorful trees frame the falls beautifully.
- Height of Land, Rangeley, ME -A breathtaking scenic overlook offering panoramic views of Rangeley Lake and the surrounding mountains. This is a must stop for sweeping foliage vistas.
- Pro Tip: Visit in the late afternoon for golden light over the mountains and lakes – perfect photo timing.
- Pro Tip: Visit in the late afternoon for golden light over the mountains and lakes – perfect photo timing.
- McLaughlin’s Lobster Shack, Lincolnville, ME – A no-frills spot for classic Maine lobster rolls, clam chowder, and fried seafood. A perfect way to wrap up the day before heading into Bar Harbor.
Day 5 – Acadia National Park
Acadia is the crown jewel of this trip – rocky coastlines, crashing waves, and trails lined with golden leaves. Even with just a day, you’ll get a taste of why this park is unforgettable. Sunrise to sunset here feels like pure magic.
- Wonderland Trail – A flat, family-friendly trail that winds through forest before opening up to the rocky shoreline. Best enjoyed at low tide when you can explore tide pools.
- Ship Harbor Nature Trail – Another easy loop offering quiet forest paths that lead to dramatic coastal views. Together, these two short hikes provide a perfect introduction to Acadia’s diverse scenery.
- Dinner at The Claremont Hotel – A historic waterfront hotel just outside of Acadia. The in-house restaurant, The Little Fern, serves elevated New England cuisine in a cozy, upscale setting. Perfect for a post-hike dinner and cocktails.
- Pro Tip: Reserve in advance -the restaurant fills quickly during peak foliage season.
- Pro Tip: Reserve in advance -the restaurant fills quickly during peak foliage season.
Day 6 – Bar Harbor – Portland – Boston
The final stretch is all about savoring those last bites of New England — lobster rolls, cozy cocktails, pumpkin patches, and historic charm. It’s the perfect way to end on a high note before heading back to reality.
- High Roller Lobster Co., Portland, ME – A creative take on lobster classics. Favorites include the lobster grilled cheese and lobster tacos. Bright, fun, and modern.
- Batson River Brewing & Distilling – Known for their inventive cocktails and cozy atmosphere. Their seasonal “Liquorwitch” cocktail is a local favorite in the fall.
- Via Sophia by the Sea, York, ME – An Italian inspired seaside restaurant where you can dine fireside. Don’t miss the beef carpaccio or lobster agnolotti.
- Connors Farm, Danvers, MA – A festive fall stop with a pumpkin patch, corn maze, and farm activities. Great for families or anyone looking to soak in one more autumn experience before heading back to the city.
- Union Oyster House, Boston, MA – End the trip at the oldest continuously operating restaurant in the United States. Their oysters, clam chowder, and colonial era ambiance make for a quintessential Boston dining experience.
- Fun Fact: Established in 1826, Union Oyster House has served everyone from Daniel Webster (who reportedly ate 36 oysters at a time) to JFK, whose booth is still preserved.
Final Thoughts
Tips for Planning
- Timing the trip:
Peak foliage typically occurs in mid-October, but the exact timing shifts each year depending on weather patterns.
- 🍁 Pro Tip: Northern states (like Maine, New Hampshire, and Vermont) peak earlier, while coastal areas and southern New England peak later. You can actually “chase” the foliage by starting north and working your way south.
- 🍁 Pro Tip: Northern states (like Maine, New Hampshire, and Vermont) peak earlier, while coastal areas and southern New England peak later. You can actually “chase” the foliage by starting north and working your way south.
- Accommodations & dining:
Book accommodations and restaurant reservations well in advance. Fall in New England is one of the busiest travel seasons.
- Expect higher prices, and know that even small motels and B&Bs book up quickly. I’d recommend reserving at least 6 months out if possible.
- Fun fact: some of the most popular inns open their October calendars a full year in advance!
- Expect higher prices, and know that even small motels and B&Bs book up quickly. I’d recommend reserving at least 6 months out if possible.
- Packing essentials:
Weather can change quickly. Days may be sunny and warm, but mornings and evenings are crisp.
- Pack layers (light sweaters, a cozy jacket, scarf, and hat).
- Comfortable walking shoes are a must for exploring trails, apple orchards, and small towns.
- Don’t forget a reusable water bottle and a day pack for hikes.
- Pack layers (light sweaters, a cozy jacket, scarf, and hat).
- Driving & roads:
You’ll be doing a fair amount of driving, often on scenic backroads.
- Build in extra drive time for leaf-peeper traffic, especially on famous routes like the Kancamagus Highway.
- Gas stations can be sparse in rural areas. Top off your tank before long scenic drives.
- Build in extra drive time for leaf-peeper traffic, especially on famous routes like the Kancamagus Highway.
- Extra touches:
- Bring cash for small-town farm stands, cider mills, and covered bridge photo stops.
