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The Perfect 10 Day New England Road Trip Itinerary

June 14, 2024

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If a New England road trip is on your bucket list, you’re in the right place! From epic hiking trails to quintessential small towns, there is so much beauty in the Northeast corner of the country.

This road trip itinerary will take you to all 6 New England states and includes a bit of hiking in each one, along with other activities. If this is your first trip to New England and you want to see a bit of everything, this is the itinerary for you!



When is the Best Time for a New England Road Trip?

In order to have nice hiking weather, I recommend doing this road trip between May and October. That’s when you’re most likely to have open trails and open businesses in the small, more seasonal towns such as Bar Harbor.

In my opinion, the best time to go on this road trip is the beginning of October, when you can witness incredible fall foliage all over New England. However, this is a really popular time, so you’re likely to experience high crowds and will need to plan further ahead with lodging. Whether you brave the crowds in the fall or prefer to visit in the summer, it’s a beautiful area in both seasons.

Tips for a New England Road Trip

  • As with any road trip, it’s a great idea to fill up on gas when you can and use an app like Gas Buddy to find the cheapest gas prices.
  • Download offline maps before you go. While I wouldn't say anywhere on this road trip is super remote, some areas won’t have the best service.
  • Both Acadia National Park and certain parking lots in the New Hampshire White Mountains take the America the Beautiful Pass. if you’re visiting other national park sites within the year, this pass will probably save you money.
  • Many places in this itinerary experience high crowds, especially in the fall. Be sure to pack your patience and have a backup plan.

10 Day New England Road Trip Overview + Map

This road trip is action-packed! Keep in mind that you’ll be doing a lot of driving if you follow this itinerary. If you prefer to take things slower, I recommend doing a longer trip or doing less things.

Road Trip Overview:

  • Day One: Drive from Boston to Acadia with stops along the way
  • Day Two: Acadia National Park
  • Day Three: Drive from Acadia to the New Hampshire White Mountains
  • Day Four: New Hampshire White Mountains
  • Days five and six: Explore Vermont
  • Day Seven: Stop in The Berkshires on your way to Connecticut
  • Day Eight: Explore Connecticut
  • Day Nine: Explore Rhode Island
  • Day Ten: Explore Boston

New England Road Trip Map

Use this map to visualize the road trip route: each day is a different color!

Day One: Boston to Acadia

Start your New England road trip by flying into Boston and renting a car! On day one, make your way to Bar Harbor, Maine. The drive by itself is just under 5 hours, but I have recommendations to break up the drive with some fun stops.

Compare rental car prices in Boston at Discovercars.com

The Salem Maritime National Historic Site at sunset
Salem, MA
Holding up a box of donuts outside of The Holy Donut in Portland, Maine
The Holy Donut in Portland, ME

First, you may want to stop in Salem, which is located just outside of Boston. Salem is most famous for the Witchcraft Trials that took place in 1692, but also has a rich maritime history. For a quick stop, check out the Salem Witch Trials Memorial, the Old Town Hall, The Witch House and the shops such as HausWitch.

From Salem, make your way to Maine and take a break in the town of Portland. This beautiful city is worth it’s own trip, but during a quick stop you should pick up some donuts from the famous The Holy Donut and perhaps head to Fort Williams Park to see the Portland Head Lighthouse.

Finally, make your way to Bar Harbor, where you’ll spend the next 2 nights. If you have enough time, catch the sunset at the Bass Harbor Head Light Station and enjoy dinner nearby at Harbor Table (my favorite restaurant near Acadia National Park). Or, explore the town of Bar Harbor and enjoy seafood at Geddy’s or the signature mac and cheese at Side Street Cafe.

Where to Stay near Acadia National Park

Day Two: Acadia National Park

Spend a full day exploring Acadia National Park! This oceanside park has over 150 miles of trails, 45 miles of carriage roads (perfect for biking) and a variety of coastal, lakeside and mountain views.

Thing To Know: Acadia is one of the top 10 busiest national parks in the country. Expect crowds, have a backup plan and make reservations when possible.

Here is how I recommend spending one day in Acadia!

Sunrise from Cadillac Mountain

Start your day by watching a beautiful sunrise from the top of Cadillac Mountain. During the winter months, this is where you can see the first light of the day from the United States! But either way, it’s a beautiful view.

A view of the sunrise from Cadillac Mountain with a cloud inversion.
Sunrise from Cadillac Mountain

You need a reservation to drive to the top of Cadillac Mountain and they can be hard to get for sunrise. I recommend being ready to book them right when they go on sale.

If you can’t snag a reservation, you can still hike to the top! There are a couple trail options to reach the top - the North Ridge and the South Ridge. The North Ridge Trail is 4.2 miles round trip while the South Ridge trail is 6.7 miles round trip. The parking is limited so make sure you arrive early enough to get a spot.

If you do get a reservation, be prepared for there to be a lot of people joining you at the top. Bring layers and a blanket to stay warm while you wait and be sure to bring a flashlight or headlamp too! It may seem crowded, but if you keep walking further from the parking lot, you should be able to find some space for yourself.

I saw an incredible cloud inversion during my sunrise and it was well worth the early wake up call!

Hike the Beehive Trail

If climbing a ladder up the side of a mountain sounds appealing to you, the Beehive Trail needs to be on your list! This iconic and unique trail has a series of ladders and steep drop offs, so you should avoid it if you’re afraid of heights. While it’s a little scary, it’s a short climb and the view at the top is very rewarding.

Looking down at a small lake surrounded by fall foliage from the Beehive Trail.Lydia climbing up ladders on the Beehive Trail
The Beehive Trail

From the peak, you’ll see the coast along with the surrounding mountains. When you’re ready to head down, do not use the ladders (it’s much safer as a one-way trail). Instead, hike down on the back trail and enjoy views of the Bowl on your way down. The hike back down is relatively easy and the entire loop is 1.5 miles.

Looking for more trail ideas? Check out my list of 14 incredible hikes in Acadia.

Hike the Ocean Path Trail

Not far from the Beehive trail, there are some beautiful coastal views along the Ocean Path. You can either hike or drive between the various viewpoints (but parking may be difficult in some areas).

The top sights along the Ocean Path are Sand Beach, Thunder Hole, Otter Cliff, Otter Point and Otter Cove. Thunder Hole is the one that I recommend most. It’s an inlet where the waves crash down in a narrow channel and make a thunderous noise during the hours leading up to high tide!

Eat at Jordan Pond House

There is a famous restaurant in Acadia located right next to Jordan Pond: the Jordan Pond House. It has been in operation since the late 1800’s and is most famous for their popovers.

Two plates of popovers and a salad from Jordan Pond House.
Jordan Pond House
Looking across Jordan Pond at two round mountains reflecting in the water.
Jordan Pond

Thing to Know: A popover is a light roll made from egg batter. It is usually baked in a special tin that gives them tall, straight sides.

Keep in mind that parking might be difficult in the middle of the day and you may have to circle around a few times. You can make a reservation or get on the waitlist. In my experience, the waitlist moved pretty quickly and you can spend a little of that time enjoying the views of Jordan Pond.

While there are a lot of options on the menu, the popovers are a must. They are fluffy on the inside and crispy on the outside, and pair perfectly with jam or butter. If you want dessert, indulge in the popover sundae - you’ll be served a scoop of ice cream inside of a popover!

If you can’t get enough of the popovers, head next door to the gift shop and purchase their popover mix to try it for yourself.

Walk to Bar Island

A unique and easy trail in Acadia is the walk to Bar Island. However, this island is only accessible during low tide, so you need to watch the tide charts accordingly (if you’re not back in time, you could be stuck for hours!) To reach the island, there is a natural land bridge you can walk across around low tide.

Looking at the path to Bar Island at low tide from the island.
The walk to Bar Island

On the island, there are a couple short trails to enjoy. You can hike to the highest point of the island where there’s a nice view of town, and admire the ruins of the former Jack Perkins Estate. The total hike with the walk over and those trails is just over 2 miles and you’ll likely see birds and sea life along the way. It’s a unique trail to add to your Acadia itinerary!

Dinner in Bar Harbor

Spend the evening enjoying dinner and exploring Bar Harbor, or head over to eat at Harbor Table if you didn’t the night before. Harbor Table is located in a different area of Mt Desert Island (about 20 minutes away), but worth the drive for the pasta and cocktails.

Day Three: Acadia to the White Mountains

On day three, road trip out of Maine and into New Hampshire. If you want to start your day with breakfast in Bar Harbor, I especially loved the cute breakfast restaurant This Way Cafe.

Looking down at a valley surrounded by mountains. There are many colorful, yellow trees and a road in the center of the valley.
Mount Willard

The drive from Bar Harbor to the New Hampshire White Mountains is a little under 5 hours.

When you arrive in the White Mountains, you may want to start with a short hike. A couple I recommend are Champney Falls, which is a 3-mile trail with a beautiful waterfall, or Mount Willard, another 3-mile hike and leads to a stunning view of the valley and road below.

After you hike, eat dinner in Lincoln or nearby. A few places I love are Gypsy Cafe (has a lot of international cuisine) and StrEatz (a food trailer with an eclectic menu).

Where to Stay in the White Mountains

Day Four: New Hampshire White Mountains

Spend the day hiking and exploring the beauty of the New Hampshire White Mountains! The Whites are a rugged mountain range that cover about a quarter of the state of New Hampshire. There is a range of trails and views for all abilities - from 4,000-foot peaks with alpine tundra to scenic viewpoints that require no hiking. This area is especially stunning if you visit during the peak fall foliage.

Hike Artist’s Bluff

If it’s your first time in the area, you will probably want to hike the famous Artist’s Bluff. This popular trail leads to a stunning view of Echo Lake and is especially lovely in the fall. Because of the crowds, I highly recommend starting your hike in the dark and watching the sunrise from the viewpoint.

A small lake seen from above, surrounded by hills full of colorful foliage.
Artist's Bluff

After watching the sunrise, make the trail into a loop by including Bald Mountain Peak (making the trail 1.5 miles). Bald Mountain is much less crowded and still has a nice view. Both trails involve some rock scrambling, so proper hiking shoes and water are essential.

For more hiking trails in the White Mountains, check out my list of the best day hikes.

Drive the Kancamagus Highway

Spend the rest of your morning driving the Kancamagus Highway (known as “The Kanc”) and enjoying some amazing views and short trails. The road is 35 miles and connects the towns of Lincoln and Conway, with many scenic vistas along the way.

Pro Tip: Download the Guide Along Audio tour of the Kancamagus Highway to learn about stops along the way while you're driving!

A waterfall flowing down some rocks that resemble a stair-stepping pattern.
Sabbaday Falls
A view of a road surrounded by colorful trees in both sides.
The Kancamagus Highway

My favorite stops on the Kancamagus Highway include:

  • Hancock Overlook, Panoramic Overlook & Pemigewasset: These three overlooks offer beautiful views of the surrounding mountains and fall colors.
  • Lily Pond: This calm pond is right on the side of the road and I saw a beautiful reflection.
  • Sabbaday Falls: You can reach Sabbaday Falls from an easy 0.7 mile trail. The unique waterfall is a bright, turquoise color and flows through a gorge that seems to make a right angle turn.
  • Rocky Gorge: This narrow gorge has a waterfall you can admire from above.
  • Lower Falls: Lower Falls is a short walk from the parking lot. It’s a great place for a picnic and popular for swimming during the summer months (exercise caution if the water is high).

There are several others to check out if you have enough time, but these are a great starting point! Read my full list of stops in my guide to the best things to do in the White Mountains.

Pro Tip: It costs $5 to park along The Kanc highway. If you have an America the Beautiful pass, that will cover the fee.

Drive to the Top of Mount Washington

Mt. Washington is the highest peak in the Northeastern United States! At 6,288.2 feet, the alpine tundra at the top provides incredible views on a clear day.

An expansive view of mountains taken from the top of Mt Washington, the highest point in the Northeast.
Mt Washington

You can reach the Mt. Washington summit by hiking, driving, or taking the unique Cog Railway, which climbs at a 25% grade. Since this is a quick itinerary, I recommend either driving or taking the Cog Railway.

I thought that the drive was really fun (and has no shortage of views). It’s a steep drive (a low gear is necessary while going back down) and has some steep drop offs.

At the peak, you can enjoy the views, shop in the gift shop, visit the museum and more. And be sure to look for the sign indicating where the fastest surface wind in the Northern and Western Hemisphere was recorded at 231 mph!

The weather can change quickly at the summit and it’s not unusual to experience high winds, fog and cold temperatures. Be sure to come prepared with warm clothing.

Day Five: Stowe, Vermont

Make your way from New Hampshire to Vermont on day five of your road trip. Stowe is a quintessential Vermont town that is especially magical in the fall.

Hike Nichol’s Ledge

If you have enough time, make the detour to hike to Nichol’s Ledge. It’s a short hike that leads to an amazing view of a lake below. And in the fall, it’s especially stunning surrounded by colorful foliage.

A view from above of a lake surrounded by colorful foliage.
Nichol's Ledge

The trail is short, but steep, and I recommend going early to beat the crowds. And make sure to avoid Town Hwy 58 when driving here if you do not have a 4x4 vehicle. Google maps may try to lead you astray!

Explore Stowe

Stowe is an adorable Vermont town full of cute shops and restaurants, and some more neat sights nearby. Here are a few things to do in Stowe and nearby:

A white church with mountains in the background and trees in the foreground.
The View of Stowe from Salon Salon
  • Drive to the top of Mt Mansfield, the highest point in Vermont! You can either hike, drive or take the gondola to reach the top. For driving, be sure to go early in the day, as the road closes early if they’ve reached capacity.
  • Walk along the Stowe Recreation Path in town.
  • Visit Moss Glen Falls, a short waterfall trail nearby.
  • Head to Salon Salon to see the best view of the Stowe Community Church.
  • Sample apple cider donuts and cider from Cold Hollow Cider Mill.
  • Take a tour (or just get ice cream and see the ice cream flavor graveyard) at the Ben & Jerry’s Headquarters.

Pro Tip: Traffic can be awful in Stowe, as there aren’t a lot of alternative routes. Pack your patience and have a backup plan!

Where to Stay near Stowe

Day Six: Woodstock, Vermont

On your second day in Vermont, tour a maple syrup farm! It’s a quintessential Vermont experience in the fall. I highly recommend visiting Baird Farm, which is located a little under 2 hours from Stowe.

Fun Fact: Vermont produces the most maple syrup in the country by far!

Tour a Maple Syrup Farm

A farm with a hill covered in bright foliage in the distance.A tree with attached tubes to collect maple syrup.
Baird Farm

Baird Farm is a family-owned business on a 560-acre farm in Chittenden, Vermont. They offer a free tour where you’ll get to walk around to see their sugarhouse, maple trees and more. Be sure to make your reservation in advance and purchase some syrup to take home (you also get free samples!)

Visit Woodstock

After your maple farm tour, head towards Woodstock, another adorable town! Here are a few things to do in Woodstock and nearby:

A view of mountains sprinkled with fall foliage seen from the top of Killington Peak in Vermont.
Killington Peak
  • Take the gondola to the top of Killington Peak, the second tallest peak in Vermont.
  • Admire the Middle Covered Bridge.
  • Try a maple cremee - Woodstock Scoops is a great place to get one!
  • Photograph the Sleepy Hollow Farm, if possible. In 2023, this view was closed during the peak fall period due to the unprecedented crowds. Be sure to check ahead of time to see if you’re allowed to visit.

Where to Stay near Woodstock, VT

Day Seven: Vermont to Connecticut

On day seven of this New England road trip, make your way south from Vermont to Connecticut, with a stop in Massachusetts along the way!

To reach Connecticut, you’ll pass through the Berkshires region of Western Massachusetts, which is very much worth exploring.

Fun Fact: The Berkshires refers to a rural region made up of small towns. It is known for a thriving arts scene, farm-to-table cuisine, waterfalls, and more.

Explore North Adams, MA

I recommend spending your afternoon in North Adams, MA. The best thing to do if you like art is to visit the MASS MOCA. This incredible contemporary art museum is housed in a former factory, so it has a very industrial vibe. It’s a huge museum where you can find works by James Turrell, Sol LeWitt, and many more. Even if you aren’t into contemporary art, I think it’s worth a visit.

For lunch, visit Greylock WORKS nearby. Housed in a former cotton-spinning mill, there are various restaurants and other businesses here. Eat at The Break Room and snag some cider to go from Berkshire Cider Project.

Looking out the window at the industrial campus at MASS Moca. There are several brick buildings and an open courtyard.
MASS MOCA
A waterfall cascading down rocks along a small stream in the forest.
Ender's Falls

Stop at some Waterfalls in Connecticut

Next, continue onto Connecticut. As you drive to Hartford, you may want to stop at a few beautiful waterfalls on the way. Enders Falls and Campbell Falls are two 1-mile waterfall trails that offer some beautiful views.

End your day in Hartford, Connecticut! If you have time, take a walk around Bushnell Park and enjoy dinner at Banh Meee, Republic Gastropub or Salute.

Where to Stay near Hartford, CT

Day Eight

Spend the day hiking in Connecticut, and then head to Rhode Island for your 6th state of the trip!

Hike in Sleeping Giant State Park

Sleeping Giant State Park is a popular state park known for its incredible vistas! Depending on your time and abilities, there are a couple different ways to reach the famous Sleeping Giant Observation Tower. You can take the easy, smooth trail at 3-miles round trip, or take the Blue Trail, where you’ll get to navigate through some rock scrambles and enjoy some additional epic views. It’s about the same distance, but much harder.

Lydia scrambling up the blue trail in Sleeping Giant State Park. There is a view of a valley down below in the background.Lydia standing out on a large rock formation with a steep cliff on one side in Sleeping Giant State Park.
The Blue Trail at Sleeping Giant

Fun Fact: Connecticut has 110 state parks. It ranks 10th in the country for the most state parks, despite being the 3rd smallest state.

Hike Chauncey Peak

Taken from the top of Chauncey Peak, a rocky cliff stands tall above a lake.Taken from the top of Chauncey Peak, Lydia sits on a rocky area with views of the lake and the surrounding valley behind her.
Chauncey Peak

Not far from Sleeping Giant, Chauncey Peak is another great trail for your Connecticut itinerary. A short and somewhat steep trail will lead you to a beautiful view looking down at the Bradley Hubbard Reservoir. If you make the trail a loop, you’ll also get to walk alongside the water.

Food and Drink Stops in Connecticut

If you enjoy visiting breweries, stop at the Kinsmen Taproom for pizza and drinks. Housed in a former bolt factory, they’ve done a beautiful job restoring this brewery. They have a variety of beers and some delicious pizza.

A cup of hot cider topped with an apple cider donut and whipped cream. The cider is in a green, paper cup with artwork depicting Hogan's Cider Mill.A pizza topped with veggies and a beer in a wine glass next to it on a table.
Kinsmen Brewing

As you continue your Connecticut road trip, stop by Hogan’s Cider Mill for a treat. In the fall, they offer delicious apple cider (with the option of it being spiked), apple cider donuts and more. Plus, they have a farm store and mini golf. It’s a fun place with cute decor.

Finally, make your way to Newport, Rhode Island, where you’ll spend the next day.

Where to Stay in Newport, Rhode Island

Day Nine: Rhode Island

Newport, Rhode Island is a coastal town known for its Gilded Age mansions and harbor full of yachts and sailboats. While you could tour the mansions (The Breakers is the most famous), I stuck with some more outdoorsy activities.

Ride Bikes on Railroad Tracks

Lydia sitting on a Rail Explorers bike parked on railroad tracks.A view of the front of the rail explorers bike. Several fallen leaves are surrounding the tracks.
Rail Explorer's Rhode Island

Ride a bike on railroad tracks with Rail Explorers! On the Southern Circuit, you’ll get to enjoy views of Narragansett Bay and have a waterfront picnic halfway through. The route is mostly flat and such a unique and fun adventure!

Hike in Sachuest Wildlife Refuge

Spend some time enjoying wildlife, colorful rocks and ocean views at the Sachuest Wildlife Refuge. The park is one of five national wildlife refuges in Rhode Island and provides an important stopover for migratory birds.

Lydia standing on top of a white rocks with a few colorful areas of orange. She is looking out at the ocean.An area of black and white rocks with a bit of a stripe pattern next to the ocean.
Sachuest Wildlife Refuge

You can hike a short loop trail here. I really enjoyed the striped rocks, plus I saw deer and birds. It’s a beautiful park!

Walk the Newport Cliff Walk

A must-do in Newport is to walk at least a portion of the Newport Cliff Walk. This is a 3.5-mile path that has some epic ocean views, plus you’ll get to see some of the famous historic mansions. I recommend making sure to visit the Forty Steps, where you can walk down closer to the ocean.

Looking down at reddish steps that leads down closer to the ocean. The top step reads 'Forty Steps'Black, smooth rocks on the shore of the ocean in Newport, Rhode Island.
Newport Cliff Walk

Pro Tip: Parking is tough for the Newport Cliffs. The best places to park are next to the Forty Steps or at Easton Beach. However, you can also park on the street near The Breakers and Salve Regina University and walk over from there.

After a fun day in Rhode Island, make the 1.5-hour drive to the Boston area so that you’re ready for the last day of your road trip.

Where to Stay in Boston

Day Ten: Boston

Spend the final day of your New England road trip exploring Boston, the largest city in New England. There is so much to do in Boston! It’s a very historic city full of museums and great food. If you only have a day, I recommend doing all or part of the Boston Freedom Trail.

The Boston Freedom Trail

The Boston Freedom Trail is a 2.5-mile path that leads you to 16 historically significant spots in US history. Red bricks on the ground will lead you to all of the stops.

A statue of Paul Revere on a horse in the Paul Revere Mall
Paul Revere Mall and Old North Church
Several historic graves along a path in the Copp's Hill Burying Ground
Copp's Hill Burying Ground

You can hop on a walking tour or do your own. If you do your own, use this brochure to learn about each site!

A Few Notable Stops on the Freedom Trail:

  • Boston Common, America’s oldest public park.
  • The Granbury Burying Ground, which has the gravestones of notable people including Paul Revere, John Hancock and Samuel Adams,
  • The Boston Massacre site, a large marker on the sidewalk shows where British soldiers fired on a crowd, killing 5 people, in 1770.
  • The Paul Revere House, which is the oldest remaining structure in downtown Boston.
  • The USS Constitution, where you can see inside two historic warships and visit a museum.
  • Bunker Hill Monument, which honors the first major battle in the Revolutionary War. You’ll need to climb 294 steps to reach the top.

Have Dinner on the North End

After a day of walking and exploring, eat in Boston’s Little Italy! This neighborhood has some of the oldest buildings in the city and has some amazing Italian food. A couple places I recommend are Italian subs from Dino’s Cafe or pizza from Regina Pizza. After dinner, sample famous cannolis at Modern Pastry or enjoy tiramisu at Caffe Vittoria.

For more details on how to spend a day in Boston, read my more detailed guide.

Final Thoughts

I hope this itinerary helps you plan an epic New England road trip! Visiting all 6 New England states in 10 days is action-packed, but makes for a memorable trip that will give you a wonderful taste of what this region of the US has to offer.

For more New England Travel Guides, check out these blogs:

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