10 day New England Road Trip Itinerary [Portland to Boston Drive]

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New England is a region of the northeastern United States, known for its historical significance. It’s home to some of America’s oldest cities and towns.

A New England road trip is the perfect way to see the best of the northeast coast. You can go at your own pace, stop when you want, and take in all of the sights!

In this post, the New England road trip will take you from Portland, Maine up to Acadia National Park, then back down through Portsmouth and into Boston, Massachusetts.

This New England road trip itinerary is filled with both adventures in nature and walking through urban streets and their history. There will be sufficient time spent exploring each city over the course of 10 days.

Quick Overview of the New England Road Trip Itinerary

Quick Overview of the New England Road Trip Itinerary

A list of stops on your New England Road Trip Itinerary:

  • Days 1-3: Portland, Maine (3-hour drive time on day 3)
  • Days 3-5: Acadia National Park, Bar Harbor (4-6 hour drive time on day 5)
  • Days 5-10: Portsmouth, New Hampshire, and Boston, Massachusetts
  • Airports: Portland International Jetport in Portland, Maine (PWM); Logan International in Boston, Massachusetts (BOS)
  • Transit: Rent a car for pick up at PMW and drop off at BOS

The New England Road Trip Itinerary Days 1-3: Portland, Maine

Day 1: Landing in Portland, Head Light, and Old Port

  • Land in Portland International Jetport early in the day if possible and pick up your rental car
  • You’ll want to book your stay for 2 nights in Portland
  • Today you’ll see some great highlights of Portland including the lighthouse and Old Port
  • Portland city drive time: 15-30 minutes around town, including the airport to Old Port

The best accommodation option would be to stay in or very close to Old Port. This is the historic downtown area of Portland with many cute boutiques for shopping and restaurants within walking distance.

If the prices in this area are out of your budget, I would recommend staying at an accommodation in either Portland’s East End or West End as they are both near the heart of Portland, Old Port.

Start your morning off with breakfast at Becky’s in the West End. The blueberry pancakes are DELISH, however, the omelets are also great for a high protein meal.

  • Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101
Getting breakfast at Becky's in Portland, Maine

After breakfast, head over to Portland Head Light State Park for a short hike! This is one of the most popular sites in Maine and offers incredible views out over Casco Bay.

You can even do a lunch picnic here! Wear walking shoes (or sandals if you’d like to hike down to the water) and do some rock climbing to get some beautiful pictures of the Portland Headlight.

Spend as much time as you want here–it’s so beautiful! (We came here twice!)

Pro-tip: Tie up your hair and bring a jacket as it’s pretty breezy and a little chilly here!

  • Portland Head Light State Park | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107
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In the afternoon, take an hour tour of the Wadsworth-Longfellow House which was Maine’s first house museum that opened up to the public. Longfellow was a national literary man of his time and most furnishings in his house are original or belonged to his family.

  • Wadsworth-Longfellow Museum | Address: 489 Congress St, Portland, ME 04101

After getting your history fix, you can take a walk and explore Old Port. This area has many cute boutiques and fun restaurants to try out!

Stop by The Holy Donut for a delicious snack (even multiple times over a 2-day trip) with interesting flavors such as the Maine blueberry cake donuts or chocolate sea salt flavor.

  • The Holy Donut | Address: 177 Commercial St, Portland, ME 04101

There are also so many restaurants lined up here that you can grab a quick lunch before doing all your shopping. Some recommendations include Duckfat (amazing Belgian-style fries with sauces) and The Honey Paw (ramen noodles and Asian infusion).

Or head over to the Maine Lobster Shack for a delicious lobster roll–nothing is better than this fresh-caught lobster. You can’t go wrong with the Maine Lobster Roll or the Brown Butter Lobster Roll, and try the Maine Root Soda while you’re here.

  • Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101
Enjoying a lobster roll at the Maine Lobster Company

Day 2: More of Historical Portland and Peak’s Island

  • Today you’ll get some more historical experiences of Portland and explore Peak’s Island by ferry
  • Portland city drive time: 10-15 minutes around town

The next morning, grab some breakfast at the Bayside American Cafe. With their delicious menu, you can’t go wrong – everything from Maine blueberry pancakes to Bayside eggs benedict!

  • Bayside American Cafe | Address: 98 Portland St Portland ME 04101

After breakfast, check out another museum for the history buff: reserve a ticket to spend about an hour touring Victoria Mansion, a historical landmark that is one of the oldest in the country known for its architecture and original interior design.

  • Victoria Mansion | Address: 109 Danforth St, Portland, ME 04101

After touring the mansion, grab lunch at Hot Suppa! This Southern diner (and what I would consider hipster) has delicious offerings such as the Mother Clucker.

  • Hot Suppa | Address: 703 Congress St, Portland, ME 04012

After getting a good bite in, take a 17-minute ferry to Peaks Island for some more exploring; we spent half a day here and had so much fun!

As you get off the ferry, rent a little golf cart From Mike’s Carts to get around the area. You can grab Lisa’s famous cinnamon bun at Peak’s Café as you start your cart tour.

Another stop on the road trip is Peak's Island

Use this map to help you navigate your way around Peak’s Island. Head north first so that you can end your drive on Seashore Avenue, which provides endless views of the ocean.

Partway through your drive on Seashore Avenue, you can park your cart along the road and take a short hike to Battery Steele, which used to be a military fortification now graffiti-covered.

If you have time, you can also drive around the neighborhood and check out some of the cutest coastal homes–make it a game to find the best-named house!

You can also check out the Fifth Main Museum on the island as well to learn more about the history of the Civil war and other exhibits.

Keep track of the ferry schedule so you don’t miss the last one! Before you go, grab an ice cream cone from Down Front.

  • Ferry to Peak’s Island |Address: 56 Commercial Street, Portland, Maine 04101

Day 3: Close Out Your Portland Itinerary and Drive 3 Hours Towards Acadia

  • Today you can choose your morning experience and then prepare for your drive to Bar Harbor
  • Portland to Bar Harbor drive time: 3 hours

You can pack everything the night before and check out as you leave in the morning. Start off the day by heading back to Old Port to grab some snacks and breakfast in preparation to drive out.

Since you’ll be savoring your last moments in Portland, Maine, you can choose what you’d like to do:

  • last-minute souvenir shopping in Old Port
  • taking some last looks at Portland Headlight
  • check out the Portland Museum of Art

You will want to leave Portland by 1 PM.

  • Portland Museum of Art | Address: 7 Congress Sq, Portland, ME 04101

It’s about a 3-hour drive west to your next stop so you’ll want to have all your favorites (snacks, music, and conversation topics) ready to go!

Read Next: The Perfect 3-Day Portland, Maine Itinerary

A stop on the road trip is Acadia National Park

The New England Road Trip Itinerary Days 3-4: Acadia National Park and Bar Harbor

Day 3 Continued: Getting to Bar Harbor and Settling In

  • When you arrive in Bar Harbor, check into your hotel and get some dinner in town
  • You’ll want to book a 2=night stay in Bar Harbor
  • Spend your time strolling through this charming small town
  • Portland to Bar Harbor drive time: 3 – 3.5 hours

Continue your New England road trip itinerary and head west towards Bar Harbor, where Acadia National Park Pond is located. You should arrive in the afternoon and get lots of views of lakes and beautiful nature scenes.

For accommodations, stay directly in Bar Harbor at a cute inn to get the best of your time. Keep in mind that cell service around these parts is spotty at best, so don’t be afraid to stop and ask for directions!

Since you’ll be here later in the afternoon, head into Bar Harbor which offers a small-town feel and is a fantastic place to enjoy some delicious food.

We got ice cream cones every time we went (which was only twice!). While you’re at it, make sure to buy some snacks, maybe even a sandwich lunch to enjoy while in Acadia National Park Pond the next day.

This would be the time to grab souvenirs or do some window shopping in Bar Harbor. There are so many cute boutique shops to just browse through!

Enjoying our meal at Galyn's om the patio on Bar Harbor.

For lunner (lunch + dinner), Galyn’s is a cozy little seafood restaurant in a Victoria-era house that has options for outdoor seating.

Opt to sit out on the patio and enjoy the fresh air and views while you eat your clam chowder soup. If that’s not for you, they also have small plates, fettuccine, sandwiches, and many more options to choose from. It was wonderful!

  • Galyn’s |Address: 17 Main St, Bar Harbor, ME

Day 4: Explore Acadia National Park Pond

  • Get an early start to Acadia National Park and do all the exploring on the hiking trails and beaches
  • Bar Harbor to Acadia drive time: 15 – 30 minutes going through the park
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Continue your New England road trip and get an early start to Acadia National Park Pond, which is known as the “Crown Jewel of the Atlantic Seaboard” and it’s easy to see why.

Take your time in Acadia and explore all that it has to offer, you won’t be disappointed! The mountain views are incredible, the road is scenic and well-maintained.

The weather in Acadia is usually pretty nice, but it can get chilly in the evenings. Make sure to pack layers so you’re prepared for everything! I had a light jacket with me, but by mid-day, I was getting pretty warm from sunshine and hiking.

One of my favorite hikes here is the Beehive Loop, which is a great way to get acquainted with the difficult trails.

If you are looking for an adventurous hike, this 450ft cliff trail will get your heart pumping! As one of Acadia’s most popular hikes, expect steep granite staircases that challenge even experienced backpackers (think ladders and iron rungs), as well as exposed cliffs. The trail is about 1.4 miles roundtrip and can take anywhere from 1-3 hours.

Another more moderate hike is the Bubble Trail which branches into North and South.

Both trails are reasonable, but if you’re looking for a shorter trail, take the Bubble Rock trail to see “the bubble,” which is a huge rock shaped like a bubble sitting precariously on the cliff of the mountains.

If mountains aren’t your thing and you’re more of a beach lover, Sand Beach and Echo Lake Beach are great for swimming and hanging out. You’ll most likely come across Sand Beach first if you’re coming from the entrance at Bar Harbor, which will also bring you to the trailhead of the Beehive Loop.

At the beach, you can unpack your lunch and enjoy a nice view out into the ocean with the sun keeping you warm.

However, if you are hungry after your hiking expedition, enjoy lunch at Jordan Pond House where you can dine on traditional meals of New England that include lobster rolls, chowder, and more.

A popular fare here is popovers and tea and if you are like me who had no idea what a popover is… it’s a light roll made of egg batter and can be eaten with whipped cream or jam and tea. Delish!

  • Jordan Pond House | Address: 2928 Park Loop Rd, Seal Harbor, ME 04675
Eating some popovers at Jordan Pond House in Acadia National Park.

For more adventuring in Acadia, make the drive to Cadillac Mountain or Thunder Hole. Cadillac Mountain is the tallest mountain on the East Coast at just over 1,500 feet with unparalleled views over Frenchman Bay and beyond.

Finally, no road trip to Acadia National Park is complete without a stop at the famous Thunder Hole! Don’t forget your raincoat because it looks like thunder when waves crash into rocks down below, causing an amazing sound experience for visitors nearby.

After a long day exploring Acadia National Park head back towards Bar Harbor at night to enjoy dinner in town. Grab a seat at one of my favorite restaurants, the family-owned Side Street Cafe.

The staff is so welcoming and the restaurant really fosters an atmosphere of community. Everything here is amazing–from appetizers to sandwiches and burgers.

  • Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609

After all the energy spent at Acadia, get some much-needed rest before the long 5.5-hour drive to Boston!

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The New England Road Trip Itinerary Days 5-10: Boston, Massachusetts (with a stop in Portsmouth)

Day 5: Make the 5.5-hour drive South to Boston, with a short stop in Portsmouth, NH

  • Check out of your rooms and prepare for a long drive south to Boston
  • You’ll want to book your rooms in Boston for 5 nights
  • Bar Harbor to Bass Harbor Light Station Drive time: 30 minutes
  • Bar Harbor to Portsmouth Drive time: 3 hours, 55 minutes
  • You’ll make a lunch stop in Portsmouth and get the chance to explore for a short while
  • Portsmouth to Boston drive time: 1 hour

As you continue your New England road trip itinerary and start your drive down to Boston, you can make a stop at Bass Harbor Light Station. This historic lighthouse is off the beaten path but definitely worth checking out if you would like to add another lighthouse to your list!

After taking some pictures of the lighthouse, continue on your New England road trip and make a stop in Portsmouth, New Hampshire.

With a population of approximately 21,000 people, Portsmouth is the 13th largest city in all of New England! It’s also home to the Strawberry Banke Museum which consists of 11 historic homes and buildings dating back as early as 1695.

You can grab lunch in Portsmouth from places like the Clipper Tavern, The Wilder, or The Franklin.

If you’re game for ice cream (which is always on my list), check out Annabelle’s Natural Ice Cream, made with only the best ingredients! Then take a walk down the main street and explore the town on foot.

  • Annabelle’s Natural Ice Cream | Address: 49 Ceres Street, Portsmouth

You’ll see an iconic New England church and steeple right in the town center. Right along this street are some cool shops like the River Run Bookstore, a fun game store called Diversions and Games, and a cute international boutique shop, Ten Thousand Villages.

After walking through some shops and exploring a little in Portsmouth, hop back in the car and finish out your New England road trip in Boston!

Next up on your New England road trip: Boston!

Driving around Boston can get congested during peak traffic hours, which will make your trip take longer than expected if you don’t plan accordingly.

Because of that, we decided to stay outside of Boston proper. Our Airbnb was about a 30-minute drive to Boston, which was actually more cost-effective for us since we weren’t always going to be in Boston proper.

If you would prefer to stay in Boston, you may be able to save on driving time on the congested roads.

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Day 6: Walk the Freedom Trail

  • You’ll explore the freedom trail on foot and really get to see all the history in Boston proper – prepare yourself, it’s a long day of walking!
  • Boston city drive time: 15-30 minutes depending on your stay

Take the rest of the days and go at your own pace. In this section of the New England road trip, you will not be driving across state lines or going long distances anymore.

There is SO much to see that you’ll need to make your itinerary work for you! Consider your top historic sites and your level of energy for all the walking you might do in the city. With that said, let’s jump into exploring Boston!

Boston is home to so much history! On the top of your list to do in Boston, the Freedom Trail.

This trail is a must-see for anyone who visits the city! The Freedom Trail is a self-guided historic walking trail that leads you to 16 of Boston’s most iconic landmarks. It is 3 miles long and will take you a whole day to complete as you make stops along the way.

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You’ll want to get started on the Freedom Trail in the Boston Commons (1). From here, you can visit the information center to get yourself a map and ask any questions. You’ll know you’re on the trail by following the marked trail embedded in the sidewalk.

As you get started, you’ll see the Massachusetts State House (2) located on a hill, and following that will be Park Street Church (3), which was one of the first landmarks travelers would see coming into Boston.

Next, you’ll come upon the Granary Burial Ground (4), which has some of the most influential historic persons like Benjamin Franklin’s parents, Paul Revere, and John Hancock. After this you’ll come upon a small square where you can visit King’s Chapel & King’s Chapel Burying Ground (5), which is America’s oldest running pulpit – the bell still rings to call worshippers into the church.

You’ll also see Benjamin Franklin’s statue (6), the Old Corner Bookstore (7), and the Old South Meeting House (8) where the Boston Tea Party began!

At this point, you are right in the middle of a commercial hub to grab lunch – we got the familiar and ordered a burrito at Chipotle. However, there are so many restaurants to choose from.

Continue your trek on the Freedom Trail after lunch to the Old State House (9), which is Boston’s oldest standing public building.

The trail will then take you to the site of the Boston Massacre (10) of 1770 where the Redcoats and Boston civilians broke out in gunfire. You’ll see the site marked with a marker.

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Next up is Faneuil Hall (11), the “home of free speech” and “cradle of liberty,” you’ll see the popular golden cricket weather vane. It is now a cool marketplace and is one of Boston’s most popular attractions!

There is something for everyone with its many shops, restaurants, and music venues all in an old-fashioned market atmosphere. Right outside the marketplace, you might spot jugglers and dancers giving a great show!

After a little shopping, you’ll continue walking towards Paul Revere’s home (12) where you can take a tour inside. Continue your trek on the Freedom Trail to the Old North Church (13), where you’ll see a statue of Paul Revere – this was the site of his midnight run.

You can also grab a snack in this area at Mike’s Pastries as he has some of the most delicious cannolis (address mentioned below)!

After the Old North Church, you’ll come to Copp’s Hill Burying Ground (14), which is the final resting place for many artisans and craftsmen in the North End of Boston.

You’ll then take a 20-minute walk towards the USS Constitution (15), which is the oldest commissioned warship afloat that fought during the war of 1812. Today, it is managed by the US Navy. You can purchase tickets and actually walk on the ship and even go underdeck to see the cannons and rooms.

Finally, head towards the last site of the Freedom Trail, Bunker Hill Monument (16), which is a 221-foot granite obelisk.

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At this point, it is likely that you’re well into the afternoon so I would recommend booking an Uber to drive you back to the Boston Commons, which is most likely where your car is parked.

If you would rather continue walking, you could walk the 3 miles back towards the commons.

From here, you can choose a place to grab dinner and call it a night! You’ll be exhausted from all the walking and sightseeing you’ve just completed.

Day 7: Whale watching, Boston Harbor, and the North End

  • After all the walking yesterday, take it easy and go whale watching
  • Explore the Italian district of the North End
  • Boston city drive time: 15-30 minutes depending on your stay

Boston is the perfect place for whale watching! There are several tour companies along the water where you can book a trip to see the whales.

The best time to see the whales in Boston is during the months of May – October when the whales migrate during the warmer temperatures.

Book your Boston whale watching tour here: City Cruises

City Cruises has experienced marine biologists and tour guides to give you information while you are on the cruise. They are also the experts in knowing the best spots that whales like to hang out.

Generally, you’ll meet up at the New England Aquarium to get in line for the tour. On our whale watching expedition, we went to Stellwagen Bank National Marine Sanctuary.

It took a few minutes of watching, but we did spot some whales!

A whale-watching tour can take anywhere from 3-4 hours. Wear a jacket as it will get cold when you’re in the middle of the ocean.

  • New England Aquarium | Address: 1 Central Wharf, Boston, MA 02110

After your tour, you’ll be right in the Boston Harbor. From here, you can walk along the waterfront and explore some sites. You can relax at the Charles River Esplanade which is a walking path along the waterfront with plenty of benches.

If you would like some more Boston history, check out some of the museums such as the Museum of Science, the Boston’s Children Museum, or the Boston Tea Party Ships and Museum.

For dinner, head to the Italian quarter in the North End which is the oldest neighborhood in Boston and has some of the most delicious food.

If you’re not into Italian food then there is still plenty of great places to try out including sushi, burgers, or lobster rolls that are sure to please everyone in your road trip group!

For dessert, try out the cannolis at Mike’s Pastry as they have been making these delicious pastries since 1926. The lines can look intimidating as they go out the door, but it goes quickly and the staff is very aware of your status in line.

  • Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113

Day 8: Harvard University and Candle Pin Bowling

  • Explore the college town of Harvard University
  • Have fun candlepin bowling
  • Boston to Cambridge drive time: 30 minutes – 1 hour depending on your stay

Boston is also home to many amazing colleges and universities. On this day of the New England road trip, we chose to take a visit to Harvard.

Start off by grabbing brunch at Le’s Vietnamese restaurant then check out the historic Harvard Bookstore.

After this, we wanted to take a walk around the Harvard Campus. Do note that visitors aren’t allowed within the buildings without a guest pass.

We just walked around the campus and noted the buildings as well as the plaques that were displayed. It was pretty cool to say that we went to Harvard!

If you’d like to experience Harvard University more deeply, you can book a 70-minute student-led tour to see everything the university has to offer. Either way, you’ll want to make sure that you don’t miss out on visiting Harvard Yard.

Book your Harvard Walking Tour

There are also three art museums and the Harvard Museum of Natural History to explore.

For a more relaxed New England activity, go candlepin bowling at Sacco’s bowling alley in Sommerville, which is about a 10-minute drive from Harvard University.

This type of bowling is a little different than what you might be used to. Candlepin bowling is played with smaller balls and the pins are thinner as well; it tends to result in more strikes which means more points!

Sacco’s does offer food for purchase so we ordered flatbreads off their menu for dinner.

  • Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144
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Day 9: Fenway Park, New England Holocaust Memorial, Boston Public Market, Cheers, and a Ghost Tour

  • Revisit Boston proper: there is so much more to see that might have been missed on the Freedom Trail – take your last day to visit all those last sites
  • Boston city drive time: 15-30 minutes depending on where you stay

I’m not much of a sports fan, but I really enjoyed a walk around Fenway Park where the Red Sox play.

It was built back in 1912 and has been around ever since, also displaying members of the team around the stadium. With a guided tour, you’ll be able to visit the stadium’s collections of photographs, artifacts, and more!

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Boston also has a memorial for the persecuted Jews during the Nazi regime where you can visit the New England Holocaust Memorial.

After walking through the memorial, you’ll end up near the Boston Public Market, which is filled with produce and gourmet food. This is the perfect spot to grab lunch!

  • New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
  • Boston Public Market | Address: 100 Hanover St, Boston, MA 02108

If you’re a huge literary fan, you can visit the Edgar Allan Poe statue, which is so descriptive and very well-made. You can see one of his most notable works: The Tell-Tale Heart. The statue stands right across the street from the Boston Commons south of Boyleston Street.

Another iconic stop in Boston is to visit the Cheers restaurant filled with memorabilia from the show! It’s located on the other side of the Boston Commons where Edgar stands. You can grab dinner here and reminisce about the show.

  • Cheers restaurant | Address: 84 Beacon St., Boston, MA 02108

For the brave, book a ghost tour of Boston’s most haunted locations! The tour guides are historians, so you can be sure that the stories they tell will be accurate and interesting-we learned so much about the cemeteries and ghost sightings!

Fun fact: there’s a little girl who is regularly spotted right next to these gravestones!

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Side Note: You can also spend one night in a historic hotel or B&B. Some of these places date back to the 1800s! Most hotels even offer their own ghost tours if you’re feeling brave enough to stay overnight at one of their historical spots.

As you hang out later in Boston, you can see the Massachusetts State House beautifully lit up in the night sky! You can grab dinner to go and have a picnic in the Boston Commons, which is a huge park area.

Day 10: Check out and return home

  • Boston to Logan Airport drive time: 15-30 minutes depending on your stay

After exploring all you can in Boston, it’ll be time to head back home. Return your car to Logan International Airport and from there fly out to your home airport.

Summary of the 10 Day New England Road Trip Itinerary

Day 1:

  • Breakfast at Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101
  • Explore Portland Headlight | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107
  • Get your history in at Wadsworth Longfellow’s place | Address: 489 Congress St, Portland, ME 04101
  • Shop in Old Port and get a snack at the Holy Donut | Address: 177 Commercial St, Portland, ME 04101
  • Grab food at the Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101

Day 2:

  • Breakfast at Bayside American Cafe | Address: 98 Portland St Portland ME 04101
  • Check out more history at the Victoria Mansion | Address: 109 Danforth St, Portland, ME 04101
  • Grab a Mother Clucker at Hot Suppa | Address: 703 Congress St, Portland, ME 04012
  • Take the Ferry to Peak’s Island | Address: 56 Commercial Street, Portland, Maine 04101

Day 3:

  • Spend your morning experiencing the last of Portland: revisit Old Port, Portland Headlight, or explore the Portland Museum of Art
  • Prepare snacks and drive 3 hours to Bar Harbor, where Acadia National Park is located
  • Arrive and check into your accommodation in Bar Harbor
  • Grab lunner at Galyn’s | Address: 17 Main St, Bar Harbor, ME
  • Do some shopping and strolling in Bar Harbor – get some snacks for Acadia
  • Get some rest!

Day 4:

  • Start early – do a difficult hike on the Beehive Loop Trail or a moderate one on the Bubble Trail
  • Eat snacks or your packed lunch at Sand Beach or Echo Beach
  • Grab lunch or some popovers and tea at Jordan Pond House | Address: 2928 Park Loop Rd, Seal Harbor, ME 04675
  • Drive to Cadillac Mountain and enjoy the views and Thunder Hole to check out the cliffs
  • Finish your day in Bar Harbor at the Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609

Day 5:

  • Stop at the Bass Harbor lighthouse then make your 4-hour drive to Portsmouth, NH
  • Grab lunch and ice cream – do some walking and shopping in Portsmouth
  • Continue your New England road trip to Boston – check into your hotel
  • Grab dinner – we got take out pizza at a corner store and rested from our long drive

Day 6:

  • Explore the Freedom Trail by walking to each site (3 miles long, but will take all day)

Day 7:

  • Go whale watching at the Stellwagen Bank National Marine Sanctuary
  • Explore the Boston Harbor: Charles River Esplanade, Museum of Science, Boston Children’s Museum, or Boston Tea Party Ships and Museum
  • Check out the Italian Quarter in the North End
  • Grab dessert at Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113

Day 8:

  • Explore the college town of Harvard in Cambridge: Harvard Yard, Harvard Bookstore, Art Museums, Harvard Natural History Museum
  • Experience New England candlepin bowling at Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144

Day 9:

  • Check out the iconic Fenway Park where the Red Sox play
  • Walkthrough the New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
  • Grab lunch at the Boston Public Market | Address: 100 Hanover St, Boston, MA 02108
  • Revisit Boston Proper – Edgar Allen Poe, and walking ghost tour, picnic in Boston Commons, do more shopping at Faneuil Hall Marketplace
  • Grab dinner at the Cheers Restaurant | Address: 84 Beacon St., Boston, MA 02108

Day 10:

  • Check out and return home

Map of the 10-Day New England Road Trip Itinerary

Options to Extend Your New England Road Trip Itinerary

If you have more time to spend on a New England road trip, here are a few other historic cities to stop: Concord, Massachusetts, New London, Connecticut, or Providence, Rhode Island.

Concord, Massachusetts is also full of culture, museums, galleries, and shops. This was also the home to writers such as Emily Dickenson and Henry David Thoreau.

Providence, Rhode Island is a small city with a lot of history and very friendly people. Be sure to check out the historic downtown area and the amazing restaurants.

New London, Connecticut where you can visit the U.S Coast Guard Academy, Fort Trumbull State Park, and many more historical landmarks.

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What to pack for your 10-Day New England Road Trip

Keep in mind that you’ll be in the car for a few hours, so also pack some comfortable clothes for a long New England road trip. Boston can also be rainy, so you’ll want to make sure to have a rain jacket and/or water-resistant shoes for all the walking you’ll do.

Here is my recommended list:

Ending Your 10-Day New England Road Trip Itinerary

That’s a wrap on the ultimate 10-day New England road trip itinerary. New England is a beautiful destination with many historical landmarks, incredible coastal views, and delicious food!

Have you traveled to New England? Are there areas that I might have missed? Comment below.

Here’s more travel inspiration you might enjoy:

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My Favorite Travel Tips + Resources

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page.

  • Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare them with Expedia (for reward points) and Skyscanner (for the lowest prices) before I book.
  • Accommodations: I love budget-friendly rentals or booking at a hotel where I can earn points. For hotels, I go through Booking.com or book directly with Marriott (for points + rewards). When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays. For vacation rentals, I usually look through Airbnb, but you could also use Vrbo. Expedia also has some great bundles for hotels, flights, and car rentals altogether.
  • Transportation: For travel in the United States, I love renting through Expedia with Enterprise or Thrifty. They have been consistent and provide the best customer service. For international travel, I’ll book through Rome2Rio or Eurail for trains or bus fares.
  • Travel Credit Card: I book all my travel (flights, hotels, car rentals) through my favorite travel credit card. I also use this card for everything on my trip including dining, excursions, and souvenirs. Apart from earning 5x more points towards free travel, there are amazing benefits: no foreign transaction fees, trip cancellation/interruption insurance, trip delay reimbursement (so I can book worry-free), fraud protection, emergency assistance – it’s really a great deal! Check it out here!
  • Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
  • Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide. I also love LastMinute.com for very affordable tickets to theaters and other experiences in Europe.
  • What to Pack: I almost always travel by backpack. For products I like, check out my packing guide page for all the things I take with me on different trips.


  1. I agree! The best time to see those beautiful colors are late September through October!

  2. Hi Tamara, thanks for stopping by! And yes, I’m also on the west coast (CA), and seeing those lighthouses was so enlightening! Portland, ME especially is beautiful!

  3. Your photos are amazing; I want to see the real thing so bad!
    I’m on the other side of the country–near Portland, Oregon–and I’ve taken a trip up the West Coast to see all of the lighthouses here. Now an East Coast trip is definitely on my bucket list! <3

  4. Hi Genia,
    Thanks for stopping by! And yes, me too with all the pretty fall colors!

  5. Great info, makes me want to be there rightnow

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