7 Day New England Road Trip Itinerary (From Boston)

If you’re dreaming of crisp air and charming small towns, this 7 day New England road trip itinerary is exactly what you need. Starting and ending in Boston, this scenic loop takes you through the heart of Vermont, New Hampshire, and Maine. This is the perfect itinerary for soaking in fall foliage, indulging in apple cider donuts, and wandering through picturesque villages (but it’s pretty fantastic any time of the year, too!)

I grew up in the Northeast (and later lived in Boston) and New England remains one of my favorite places to road trip. The combination of mountain hikes, historic inns, and cozy coastal towns is unbeatable.

In this article:

• A complete 7 day New England road trip itinerary from Boston
• Map of the best New England fall foliage route
• Must-see stops and scenic drives in Vermont, New Hampshire, and Maine
• Tips on where to stay, eat, and explore

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7 Day New England Road Trip Itinerary Map

Here’s a detailed 7 day New England road trip itinerary map to help visualize your journey. I’ve labeled activities by icon and color-coded the map by day:

This route covers roughly 900 miles and includes key fall highlights: Woodstock, Stowe, Burlington, Franconia Notch, the Kancamagus Highway, Acadia National Park, Bar Harbor, and finally Boston.

If you’re looking for a shorter road trip, check out this 3 day Boston to Maine road trip itinerary.

Day 1 – Vermont Charm: Woodstock & Stowe

This New England road trip departs from Boston – which is the easiest and most convenient airport to fly into for your trip. It also tends to have the most direct flights and least expensive airfare.

After arriving in Boston, pick up your rental car (or campervan rental!) and head up to Stowe and Burlington, Vermont. You’ll pass through Woodstock on your way.

TIP: I recommend booking your rental car with Discover Cars. They search across the major rental companies to find the best rate and let you cancel for free up to 48 hours before pickup, so you can grab a good rate now without stressing if your plans change.

Morning: Drive from Boston to Woodstock

🚗 Drive Time: About 3 hours

Kick off your New England road trip itinerary from Boston with a scenic drive through Massachusetts and into the heart of Vermont. I recommend getting an early flight into Boston so you can maximize your time in Woodstock.

Vermont is one of my favorite places to visit. It’s wonderful during the summer, but it’s especially magical in the fall when all the leaves are changing colors.

Afternoon: Explore Woodstock’s Covered Bridges & Cafes

Take your time exploring Sleepy Hollow Farm (one of the most photographed spots in Vermont), Quechee Gorge (Vermont’s little Grand Canyon), and hike Mount Tom for sweeping views.

Grab lunch at Mon Vert Cafe or Soulfully Good Cafe and wander through local shops like Yankee Bookshop.

NOTE: The road to Sleepy Hollow Farm is only accessible to local traffic in the fall due to crowds.

Woodstock is the type of town that feels like a movie set; complete with historic homes, friendly locals, and trees bursting with color in the fall. You can easily spend half a day here.

Evening: Scenic Route 100 to Stowe

🚗 Drive Time: About 2 hours

From Woodstock, drive along scenic Route 100 to Stowe, passing through small towns and vibrant foliage. This road is famous for its covered bridges and countryside charm.

In Stowe, stroll the downtown shops and grab dinner at Piecasso or Butler’s Pantry.

TIP: If you’re short on time, driving Rt-89 between Woodstock and Stowe will save you about 40-minutes, but is less scenic.

🛌 Where to Stay: Stowe Village Inn or Green Mountain Inn in historical downtown Stowe

Day 2 – Burlington & Lake Champlain Adventures

After 5 hours of driving on the first day, this day starts easy with a casual (and short!) drive through beautiful Vermont to Burlington and Lake Champlain. I’ve been to Burlington several times and love it’s relaxed vibe and cozy coffee shops.

Morning: Church Street & Lake Views

🚗 Drive Time: About 45 minutes from Stowe

Spend your morning in Burlington, a lively college town nestled on the shores of Lake Champlain. Church Street Marketplace is a great place to wander through local boutiques and street performers. Stop by the ECHO Lake Aquarium or enjoy a relaxing walk along the waterfront.

Afternoon: Local Flavors & Shopping

Grab lunch at Hen of the Wood or The Farmhouse Tap & Grill. They’re both excellent farm-to-table spots.

Afterward, browse unique shops like Common Deer or The Vermont Flannel Company. Don’t forget to pick up some chocolates (and hot cocoa!) from Lake Champlain Chocolates.

If you’re traveling in early October, Burlington’s fall colors peak along the shoreline and parks. End your day with a lakeside sunset or a short brewery tour.

🛌 Where to Stay: Hotel Vermont or Blind Tiger Bed & Breakfast

Day 3 – Franconia Notch

Now it’s time to start making your way to the east coast. But first, drive to New Hampshire and head towards the White Mountains for a day.

Hike Flume Gorge or Artists Bluff

🚗 Drive Time: About 2 hours

Leave Vermont behind and head southeast to New Hampshire’s White Mountains. Your main destination is Franconia Notch State Park, where you’ll find two of the best fall hikes in New England.

Start with the Flume Gorge—a stunning 2-mile loop trail through a narrow granite gorge with waterfalls and covered bridges ($18 pp fee). Then, head over to Artists Bluff, a short yet steep loop trail with beautiful views of Echo Lake.

Other Highlights

• Ride the Cannon Mountain Tramway to the summit
• Visit The Frost Place, home of poet Robert Frost
• Grab pancakes at Polly’s Pancake Parlor or dinner at Cold Mountain Cafe

🛌 Where to Stay: RiverWalk Resort or Sugar Hill Inn

Day 4 – Kancamagus Highway & White Mountains

The White Mountains region is a must-see on any New England fall road trip, and today’s route offers unbeatable views as you wind through the scenic Kancamagus Highway.

Morning: Kancamagus Highway

🚗 Drive Time: About 1.5-2 hours

This is the day everyone looks forward to on a fall road trip: the Kancamagus Highway. This 34-mile stretch of Route 112 offers some of the best fall foliage in the country.

Kancamagus Highway connects Lincoln to Conway, New Hampshire. There are many stops and hikes along this drive, so plan for some extra time to enjoy the views!

NOTE: During peak foliage season (usually October) traffic can be much slower on this road, sometimes taking double the time.

Best Kancamagus Highway Stops:

• Sabbaday Falls Trail – A short, easy 0.7-mile hike to a waterfall.
• Boulder Loop Trail – A moderate 3.1-mile loop with views.
• Champney Falls Trail – A moderate 3.1-mile hike to waterfalls, with the option to extend to Mount Chocorua for 9 miles total.
• Greeley Ponds Trail – A moderate 7.6-mile hike to two scenic mountain ponds.
• Rocky Gorge Scenic Area
• Albany Covered Bridge (a short detour)

I have a complete guide to driving Kancamagus Highway in New Hampshire here!

Plan to spend a few hours stopping at these lookouts and short hikes. This highway delivers nonstop color and is an essential part of your 7 day New England road trip itinerary!

Afternoon: Explore North Conway Town & Trails

After finishing the drive, head into Conway. Visit Diana’s Baths for a short hike to waterfalls, or stop by Echo Lake State Park. If you’re into trains, the Conway Scenic Railroad is a nostalgic ride through mountain passes.

Grab lunch at Peach’s or dinner at Black Cap Grille, and don’t leave without a treat from Bavarian Chocolate Haus!

🛌 Where to Stay: Fairfield Inn & Suites or Golden Gables Inn

Day 5 – Acadia National Park & Bar Harbor, Maine

With a little under 5 hours of driving on day 5, I recommend getting an early start so you can maximize your time at one of the best National Parks on the east coast – Acadia!

Park Loop Road And Jordan Pond

🚗 Drive Time: 4.5 hours from North Conway to Bar Harbor

Head east to Bar Harbor, your base for exploring Acadia National Park. Start your visit by driving along the scenic Park Loop Road, then hike around Jordan Pond. The Jordan Pond House is a great lunch stop and famous for its popovers.

Other sites to check out on Park Loop Road:

• Sand Beach
• Thunder Hole
• Otter Cliffs

After, rent an e-bike and explore Acadia’s carriage roads, or head into downtown Bar Harbor.

🛌 Where to Stay: Bar Harbor Manor, Acadia Inn, or Bar Harbor Grand Hotel

Day 6 – Acadia Sunrise & Coastal Route to Boston

Day 6 offers one last chance to soak in the charm of Bar Harbor and enjoy the relaxing pace of Maine’s coastal towns before heading back to Boston to wrap up your 7 day New England road trip.

Morning: See The First Sunrise In The US At Cadillac Mountain

I highly recommend getting an early start so you can catch sunrise at Cadillac Mountain. This is the first spot in the United States where you can see the sunrise!

NOTE: Reservations are required to drive to Cadillac Mountain from late May to late October. The cost is $6 per vehicle and can be made at the recreation.gov website. Tickets are released 90 days ahead and 2 days ahead – and they usually sell out in minutes so set a calendar reminder!

Drop by Choco-Latte Cafe in Bar Harbor before you hit the road and get one of their homemade bagels and a latte.

Afternoon: Scenic Drive Along Coastal Maine

🚗 Drive Time: 5 hours from Bar Harbor to Boston (via coastal Route 1)

Instead of rushing back, take the coastal route and stop in Camden or Rockland. These small towns are full of lighthouses, harbor views, and lobster shacks. Portland, Maine is also a great detour if you’re into food and microbrews.

This route is especially scenic if you’re looking for a more laid-back finale to your 7 day New England fall road trip itinerary.

Evening: Downtown Boston

Once you arrive in Boston, check into your hotel and then head to the North End for some fantastic Italian food! The North End is one of my favorite areas to wander around in Boston. There’s some great restaurants (like La Famiglia and Trattoria) but it’s also impossible to make a bad choice – just drop in somewhere that looks good!

After, pick up a cannoli from Modern Pastry (they’re better than Mike’s Pastry in my opinion!) and then head to the waterfront for a casual stroll.

🛌 Where to Stay: The Verb Hotel or The Godfrey Hotel Boston

Day 7 – End Your Trip in Historic Boston

After six days of exploring the countryside, cozy small towns, and coastal gems of New England, it’s time to wind down your road trip with a day in one of the country’s oldest cities. Boston is both walkable and packed with history, so it’s easy to soak in a lot during your final hours.

Morning: Freedom Trail, Beacon Hill, or Harvard Square

Back in Boston, spend your final day exploring iconic neighborhoods, like Beacon Hill and Back Bay. Walk the Freedom Trail, or relax in Harvard Square or Boston Common.

I used to live in Boston and there’s so much to do in the city – I especially like that it doesn’t feel as overwhelming as NYC.

Alt Option: If you’re visiting in late October, check out the best things to see in Salem MA (30 minutes by train). Nothing beats Salem for halloween festivities.

One of my favorite sight-seeing activities in Boston is a duck boat tour. You’ll be picked up near the Boston Aquarium in an amphibious vehicle – it can drive on streets or boat through water! It’s the perfect way to see Boston, and the tour guide’s are hilarious.

If you have time, grab lunch at Tatte Bakery or visit the Boston Public Market for a final taste of New England.

Travel Tips For Planning A 7 Day New England Road Trip

There are many areas, especially in the mountains, where cell service is limited or non-existent. You may be able to get LTE service in the mountains (so calls and texts will work), but don’t count on being able to use your data.

I recommend downloading maps and confirmation emails before your trip. Google Maps offers an offline maps option in the app which saves a map of the area you select to your phones hard-drive (so you can use it even while out of cell service.)

If you’re using the GMail app you’ll be able to access emails offline, otherwise take a screenshot of any important confirmation emails for hotels or activities.

Bring some cash! Yes, cold hard cash! There are lots of roadside stands and small markets that operate on a cash-only basis.

If your New England road trip is in September or October, be prepared for longer travel times. This is the busiest time of the year in the Northeast and drive times can be double.

Make hotel reservations as far in advance as possible! Because this area is fairly remote, there aren’t a ton of hotels so during peak season it can be difficult to find availability. Plus, the earlier you book the better the rates tend to be.

Many hotels have a multi-night minimum during busy seasons. If you’re only in need of one night, try calling the hotel directly. Often times if they have an open night in between other reservations they’ll bend the rules and give you the room instead of letting it sit empty.