New England is one of the most beautiful regions in the United States for a road trip. Covered bridges, mountain scenery, historic towns, coastal villages, and scenic byways combine to create a journey that feels very different from one day to the next. This 5-day New England road trip itinerary travels through five states, offering a mix of outdoor adventure, small-town charm, and classic regional attractions.
It’s a busy itinerary, but one where the journey takes you places to enjoy along the way and isn’t just transit. Covering nearly 900 miles / 1500 kms, this road trip covers all 6 of the New England States, but only briefly. To get more comprehensive cover, we definitely recommend 10-14 days in the region.
Day 1: Kancamagus Highway + Fryeburg, MA + North Conway + Mount Washington, NH
230 miles / 4 .5 hours drive time
Start the road trip by heading north out of Boston towards the White Mountains. Start early to get out of Boston and into the mountains in good time. Stop at an apple cider donut shop along the 93 highway north to power up for this 2-hour drive.
Kancamagus Highway
The Kancamagus Highway is regarded as one of the most scenic drives in New England. It is especially good for leaf-peeping season!
Stretching for 34 miles through the White Mountain National Forest, the route passes forests, rivers, waterfalls, and numerous scenic overlooks.
Plan extra time for stops along the way, as there are plenty of short walks and viewpoints worth exploring.
Fryeburg, Maine
If you are wanting to check off States on this trip, make a brief detour to Fryeburg, Maine, just over the border from Conway. Grab a coffee, some souvenirs and admire the far west of this lush state.
North Conway
North Conway is in the heart of the White Mountains. The town offers a good mix of outdoor recreation, local shops, restaurants, and family-friendly attractions.
It’s a good place to stop for lunch. We recommend the Moat Mountain Brewing Company.
Mount Washington Cog Railway
At 6,288 feet, Mount Washington is the highest peak in the northeastern United States and is known for its extreme weather conditions.
You can either take the historic Mount Washington Auto Road to the summit or take the seasonal Cog Railway. On a clear day, the views stretch across multiple states and into Canada.
The summit facilities include a visitor center, museum exhibits, and observation areas.
NOTE: If the weather is bad, there is no point going to the summit, because you can’t see anything! This is definitely fair-weather activity.
Where to stay at Mount Washington
For us there is only one option – the Omni Mount Washington Resort & Spa. This grand old dame of a hotel was built between 1900 and 1902, and was made a National Historic Landmark in 1986.
The red and white building reminds me a little of the Hotel del Coronado near San Diego!
Day 2: Franconia Notch + St Johnsbury + Stowe + Montpelier + Quechee Gorge, VT
185 miles / 3.5 hour drive time
Start your day with a quick trip down to Franconia Notch – a scenic route between the Kinsman and Franconia mountain ranges.
Short stop-offs in Franconia Notch include Flume Gorge and The Basin.
If you’re running short on time, you’ll have experienced lots of the White Mountains on the previous day, so you can head straight over to Saint Johnsbury.
If you have the time – it’s a beautiful spot.
Saint Johnsbury
Often overlooked by visitors rushing through Vermont, St. Johnsbury offers a charming introduction to the state’s Northeast Kingdom region. Historic buildings, local shops, and a laid-back atmosphere make it a great stop.
We enjoyed a walk through downtown and recommend you grab a coffee at The Buttery: Kitchen + Pantry.
Stowe
Few places capture the image of Vermont quite like Stowe. Surrounded by the Green Mountains, the town is known for its classic white church steeple, and cute village center. Take a stroll Main Street, sample local maple products, or simply enjoy the mountain scenery.
Stop in to the original Ben & Jerry’s for some delicious ice cream on your way south.
Montpelier
As the smallest state capital in the United States, Montpelier offers a very different experience from most capital cities. Its compact downtown is filled with independent bookstores, cafés, and locally owned businesses. It is super cute!
The gold-domed Vermont State House is one of the city’s highlights and provides an interesting glimpse into Vermont’s history and government.
Quechee Gorge
Dubbed “Vermont’s Little Grand Canyon,” Quechee Gorge is one of the state’s most visited natural attractions. The gorge down a steep 165 feet below the bridge that spans it, creating impressive views that are easily accessible for visitors of all ages.
Several walking trails provide additional opportunities to explore the surrounding landscape.
Don’t miss a visit to Simon Pearce, a glass blower and restaurant overlooking the Quechee River. We enjoyed this place so much during our weekend in Vermont.
Where to stay at Quechee Gorge
Our hotel recommendations near Quechee Gorge include the Woodstock Inn & Resort, on the other side of Taftsville. Or the Align Inn Vermont, which is nearer the State Park.
Day 3: Mount Equinox Skyline Drive + Stockbridge, MA
163 miles / 3.5 hours drive time
Make your way south and enjoy the hospitality of Arlington, Vermont for breakfast. We loved filling up at BRONWYN on Battenkill.
It’s time to drive up the epic Mount Equinox Skyline Drive – one of the highest toll roads in New England.
Climbing more than 3,000 feet to the summit of Mount Equinox, the drive winds through forests before opening to spectacular views across Vermont, New York, and Massachusetts.
At the summit, there is an observation area and lots of panoramic mountain scenery to enjoy.
NOTE: This is a paid drive and has limited opening hours – please check before you depart.
If you don’t want to do any more scenic drives, your alternative morning activity can be visiting Hildene, The Lincoln Family Home, near Arlington VT.
Cute towns and sights to see on the way between Arlington and Stockbridge include: Old Bennington, with its monuments and historic taverns; and The Mount, Edith Wharton Cultural Center near Lenox.
Stockbridge, Massachussetts
Crossing into Massachusetts, Stockbridge is a quintessential New England village experience. Historic homes, tree-lined streets, and a walkable town center make Stockbridge an enjoyable place to spend an afternoon.
The town is perhaps best known through the paintings of Norman Rockwell, whose museum is located nearby. There is also a Gilded Age summer house, Naumkeag, which is now a museum. And The Mission House, a 18th-century missionary home and now a Native American museum.
Where to stay in Stockbridge, MA
We suggest the historic Red Lion Inn, and dinner at Michaels Restaurant nearby. Or the Quality Inn Great Barrington, which is a cute town just south of Stockbridge.
Day 4: Litchfield + Waterbury + Mystic, CT
140 miles / 3 hours drive time
NOTE: If you only have 4 days, head back to Boston now.
Day 4 will have you drive through the Berkshires – a mountain range in western Massachusetts, interspersed with cute villages and craft stores.
Alongside quaint New England villages, you’ll also find lots of State Parks and leaf-peeping opportunities for the Fall. We recommend Kent Falls State Park.
Litchfield
Litchfield is in northwestern Connecticut, and is full of historic charm. The town green, colonial architecture, and surrounding rolling hills make it one of the most attractive small towns in the state.
It’s an excellent place for a coffee stop! Try Toast & Co or @ The Corner.
Waterbury
Once known as the ‘Brass City’ due to its place in the American brass manufacturing industry, Waterbury still has lots of historic character. The most recognizable landmark is the Waterbury Union Station clock tower, designed by the same architectural firm as New York City’s Grand Central Terminal.
Waterbury offers an interesting glimpse into a different side of New England history than the small villages and rural landscapes previously passed through on this road trip itinerary.
Have lunch at Seven Villages Restaurant or House of Goats near the village green.
Mystic
Your afternoon and evening destination is the maritime heritage town of Mystic. This seaport town combines waterfront scenery, colonial history, and family-friendly attractions perfectly.
The downtown area is filled with locally owned shops, ice cream parlors, and seafood restaurants, making it a great place to spend the evening.
The Connecticut coastline is worthy of its own more in-depth exploration – it is full of postcard views and lovely seaside vibes. But on this road trip, you’ll just be getting a taster!
Where to stay in Mystic
There are lots of historic inns in Mystic, but our pick is the Whaler’s Inn – a fantastic location with parking too!
Day 5: Newport + Providence, RI
85 miles / 2.5 hours of drive time to Providence OR 130 miles / 3.5 hours of drive time all the way back to Boston.
Take the coast road along to Newport, famous for its Gilded Age mansions, ocean views, and sailing heritage.
Take a tour of a lavish estate like The Breakers, walk portions of the Cliff Walk, or explore the historic waterfront district.
Although it is full of luxury homes, you can still stop for an affordable lunch and a fun look around.
If you wanted an alternative to Newport, the less touristy Bristol offers a relaxed waterfront feel.
The shoreline is especially scenic at Colt State Park, with walking and cycling paths along the bay. Another highlight is Blithewold Mansion, Gardens & Arboretum, a historic estate with landscaped gardens overlooking the water.
Providence, Rhode Island
Providence is such a great sized city. Rhode Island’s capital city combines history, culture, and a vibrant dining scene (if you’re foodies like us). The downtown area is compact and easy to explore, so it is good for this late in the itinerary, where you may be feeling tired after a busy week.
Providence provides an enjoyable urban contrast to the small towns and natural scenery featured throughout the rest of the road trip.
The return drive to Boston is only 1 hour, so it can be done in the evening or morning, depending on your schedule.
7-Day New England Road Trip – Extras
If you have a few extra days available, consider extending your road trip with these two iconic Massachusetts destinations:
- Martha’s Vineyard – Just off the coast, Martha’s Vineyard is known for its beaches, charming villages, and relaxed island atmosphere. Explore the colorful gingerbread cottages of Oak Bluffs, enjoy fresh seafood, or simply spend time on the island’s scenic coastline. A day trip is possible, but an overnight stay allows for a more relaxed experience.
- Salem, Massachusetts – Best known for the Salem Witch Trials of 1692, Salem is so much more today! You can enjoy museums, historic sites, waterfront areas, and walking tours that bring the town’s history to life. October is the busiest time to visit (Halloween vibe), so prepare for that if you are visiting Salem in leaf-peeping season!
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