This 10-day itinerary circles through all six New England states – Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire, and Maine.
You’ll visit historic cities, charming small towns, scenic natural wonders, and indulge in local foods along the way.
Each day lays out a realistic route with must-see stops, activities, and tasty bites.
The schedule is season-neutral and suitable for all ages, with a mix of history, nature, and fun.
Buckle up and enjoy the journey!
Day 1: Boston, Massachusetts – Historic City Beginnings
Welcome to Boston! Spend your first day exploring the historic and walkable city where America’s story began.
Park the car and set out on foot along the Freedom Trail, a 2.5-mile path linking 16 key historic sites downtown.
You’ll see Boston Common (America’s oldest public park), Paul Revere’s House, and Faneuil Hall among other landmarks.
Along the way, enjoy Boston’s classic eats: perhaps a bowl of New England clam chowder or a famous cannoli from a North End bakery.
In the afternoon, stroll the picturesque Beacon Hill neighborhood with its brick row houses and gaslit lamps, or visit the waterfront New England Aquarium if traveling with kids.
In the evening, dine in the North End (Boston’s Little Italy) or at a bustling food hall in Quincy Market.
Rest up in Boston tonight – tomorrow the road trip truly begins!
Highlights:
- Freedom Trail – Walk between sites like the Old State House and Paul Revere’s House, learning early American history at each stop.
- Faneuil Hall & Quincy Market – Grab lunch from diverse food stalls and watch street performers in this lively historic marketplace.
- Beacon Hill – Wander Acorn Street and Louisburg Square for quintessential Boston charm.
- Local Eats – Try Boston’s clam chowder, Fenway Frank hot dogs, or pastries in the North End (the chocolate-dipped cannoli at Mike’s Pastry is legendary).
Day 2: Coastal Massachusetts to Newport, Rhode Island
Leave Boston in the morning and head south toward Rhode Island.
On the way, you can stop in Plymouth, MA (about 40 minutes from Boston) to see Plymouth Rock and the Mayflower II, a replica of the Pilgrims’ ship.
An hour further south brings you to Newport, Rhode Island, a beautiful seaside city famous for its Gilded Age mansions.
Spend the afternoon in Newport walking the Cliff Walk, a scenic 3.5-mile coastal path with the ocean on one side and grand historic mansions on the other.
Peek at The Breakers and Marble House – opulent Vanderbilt family summer “cottages” – and imagine the lavish lives of Newport’s 19th-century elite.
In town, explore Thames Street’s shops and galleries or visit the International Tennis Hall of Fame if interested.
Wind down your day with a fresh seafood dinner by the harbor – Newport is known for clam chowder, stuffies (stuffed clams), and lobster rolls.
Don’t miss sampling a locally made ice cream or Del’s frozen lemonade for dessert. Overnight in Newport.
Highlights:
- Plymouth (optional) – See where the Pilgrims landed in 1620. The tiny Plymouth Rock and the full-scale Mayflower II ship bring colonial history to life.
- Newport Cliff Walk – Take in breathtaking ocean views and the exteriors of mansion museums like The Breakers on this famous coastal walk.
- Newport Mansions – Tour one of the Newport Mansions (The Breakers is highly recommended) to marvel at gilded ballrooms and gardens.
- Newport Harbor – Stroll the wharves and waterfront. Enjoy seafood at a dockside restaurant – try clam cakes or a lobster dinner with a view of the boats.
Day 3: Newport, RI to Mystic, Connecticut – Mansions to Maritime
Spend the morning wrapping up Newport.
You might drive Newport’s Ocean Drive, a ten-mile scenic loop around the coastline with views of rocky shores and lavish estates.
Afterward, depart for Connecticut (Newport to Mystic is about 1 hour).
Arrive in Mystic, Connecticut by midday to dive into New England’s maritime heritage.
Mystic is a charming historic seaport town – perfect for families and history buffs alike.
Visit the Mystic Seaport Museum, the nation’s leading maritime museum, where you can explore tall sailing ships and a recreated 19th-century seafaring village.
Kids will love the hands-on exhibits and old ships (you can even board a historic whaling ship).
Next, head to downtown Mystic to see the famous Mystic River Bascule Drawbridge, which opens regularly for boat traffic.
Grab lunch at the original Mystic Pizza (made famous by the Julia Roberts film) or savor a lobster roll at a local clam shack.
In the afternoon, if time permits, drive about an hour to Hartford, Connecticut’s capital.
In Hartford you can tour the Mark Twain House & Museum, where the famous author wrote some of his classics – it’s an insightful stop for literature lovers.
Come evening, enjoy dinner in Hartford (try some New Haven-style pizza or Connecticut’s beloved steamed cheeseburger) or back in Mystic’s cozy waterside eateries.
Overnight in either Mystic or Hartford, positioning yourself for the journey north tomorrow.
Highlights:
- Ocean Drive (Newport) – A scenic coastal drive past mansions and beaches; stop at Brenton Point State Park for ocean panoramas.
- Mystic Seaport Museum – Explore historic ships (like the Charles W. Morgan whaling ship), a shipyard, and exhibits about life in a 1800s coastal village.
- Downtown Mystic – Watch the drawbridge in action and browse boutiques. Don’t miss a slice at Mystic Pizza or delicious seafood by the Mystic River.
- Mark Twain House (Hartford) – Tour the beautiful Victorian home of Mark Twain, filled with antiques and quirky decor, to learn about the author’s life and works.
Day 4: Into Vermont – Green Mountains and Quaint Villages
Get an early start for a longer drive today as you leave Connecticut and head for the Green Mountain State of Vermont.
The drive from the Hartford area to central Vermont takes about 3–4 hours.
For a scenic route, head north on I-91 and consider a stop at Quechee Gorge in Vermont, just over the border – a quick walk onto the bridge gives you a view into “Vermont’s Little Grand Canyon,” a 165-foot deep gorge.
A few miles further is the postcard-perfect town of Woodstock, VT.
Spend some time in Woodstock strolling around the village green, browsing local shops, and snapping a photo of the Middle Covered Bridge right in town.
For a taste of Vermont farm life, you could visit Billings Farm & Museum (a working dairy farm and history museum) or sample cheddar at the Woodstock Farmers’ Market.
After lunch, continue your drive deeper into the Green Mountains.
Take the scenic Route 100 north, a famed byway that winds through classic Vermont countryside.
You’ll pass rolling hills, farms, and covered bridges – this route is especially beautiful with fall foliage, but lovely year-round.
Along Route 100, consider a brief stop at Cold Hollow Cider Mill in Waterbury Center for fresh apple cider and cider donuts (a Vermont treat), or at a maple syrup farm store for some pure Vermont maple syrup.
By late afternoon, arrive in the Stowe, Vermont area, a charming mountain town that’s a four-season resort destination.
If there’s time, drive up to Stowe’s Smugglers’ Notch pass (weather permitting) to experience its dramatic cliff-lined road, or take a walk down Stowe’s picturesque Main Street.
In the evening, relax at your Stowe lodging.
Enjoy dinner at a local tavern or brewpub, and maybe treat yourself to a maple creemee (Vermont’s famous maple-flavored soft-serve ice cream) for dessert.
Highlights:
- Quechee Gorge, VT – Quick scenic stop to view the gorge and Ottauquechee River from the bridge or visitor center.
- Woodstock, Vermont – Quintessential New England village with Federal-style architecture and a photogenic covered bridge. Great spot for lunch or coffee on the village green.
- Scenic Route 100 – Drive through the heart of Vermont. Enjoy views of green mountains, pastoral landscapes, and perhaps stop at a roadside waterfall (like Moss Glen Falls near Granville) or a local craft shop.
- Stowe – Mountain town known for skiing and scenery. If time allows, drive through Smugglers’ Notch or ride the Stowe Mountain gondola (in summer it offers stunning views). Local food tip: Vermont is cheese country – try some local cheddar or visit the Cabot Farmer’s Store in Waterbury.
Day 5: Northern Vermont to New Hampshire’s White Mountains
Start the day with a sweet treat in Waterbury, VT – tour the Ben & Jerry’s Ice Cream Factory to see how this famous ice cream is made and sample the flavor of the day.
It’s a fun, quick stop (tours are about 30 minutes, and there’s an ice cream scoop shop and quirky “Flavor Graveyard” on site).
After indulging in ice cream, continue your road trip east into New Hampshire.
Your destination is the White Mountains, the rugged range spanning northern New Hampshire (about a 2-hour drive from Stowe).
Cross into New Hampshire near Franconia Notch for an afternoon of mountain scenery and fresh air.
In Franconia Notch State Park, take a short hike to the Flume Gorge, a stunning natural gorge with wooden walkways through mossy granite walls and cascading waterfalls.
Nearby, you can stop at the Old Man of the Mountain Memorial – this famous rock profile collapsed in 2003, but a viewing area with steel profilers shows how it once appeared on the cliff.
Next, drive the legendary Kancamagus Highway (Route 112) eastward from Lincoln to Conway.
The “Kanc” is a 34-mile National Scenic Byway known for its sweeping mountain vistas, especially vibrant in autumn.
Along the Kancamagus Highway, pull off at overlooks and picnic areas: Sabbaday Falls offers a short walk to a pretty waterfall, Rocky Gorge has a pedestrian bridge over rushing water, and various outlooks provide panoramic views of the White Mountain National Forest.
Keep an eye out for wildlife – you might spot a moose or black bear in this region (from a safe distance, of course).
By late afternoon, you’ll reach North Conway, NH, a tourist-friendly town nestled among the mountains.
North Conway’s Main Street has charming shops (don’t miss Zeb’s General Store for old-fashioned candies and New England goods) and views of the surrounding peaks.
In the evening, consider a casual dinner at a local pub or family restaurant – perhaps try New Hampshire maple syrup on a stack of pancakes or a hearty New England pot roast. Overnight in the North Conway area.
Highlights:
- Ben & Jerry’s Factory (Waterbury, VT) – Fun and tasty! Take the factory tour and enjoy some of Vermont’s most famous ice cream at the source.
- Flume Gorge (Franconia Notch, NH) – Walk through a cool mountain gorge with waterfalls and covered bridges; it’s about a 2-mile loop and suitable for most ages (there’s a shuttle option partway if needed).
- Kancamagus Highway – Classic road trip segment with no gas stations or hotels – just pure nature. Stop at Kancamagus Pass (the highest point of the highway) for an overlook, and enjoy picnic spots by the Swift River.
- North Conway, NH – Browse the outlet shops or visit the Conway Scenic Railroad station (if time, you could even take a short vintage train ride the next morning). This is a good place to pick up souvenirs from the White Mountains region.
Day 6: New Hampshire to Coastal Maine – Lighthouses & Lobster
Today you’ll trade mountains for the Maine coast.
In the morning, depart North Conway and drive east into Maine (North Conway to Portland, ME is about 1.5 hours).
For a leisurely route, take US-302 through the scenic lake region, passing Lovell and Bridgton – you’ll get glimpses of forests and lakes that are lovely year-round (and very popular in summer).
Arrive in Portland, Maine by late morning. Portland is a vibrant small city known for its historic port and fantastic food scene.
Spend the midday exploring Portland’s Old Port waterfront district: cobblestone streets lined with boutiques, galleries, and seafood eateries.
You can tour the working waterfront and perhaps see fishermen unloading the day’s catch. Have lunch in Portland – this is the perfect time to try Maine’s famous lobster roll (fresh lobster meat in a toasted bun, typically with butter or mayo).
Popular spots like Eventide Oyster Co. or a food truck by the wharf serve up delicious lobster rolls and chowder.
After lunch, drive a few minutes to Cape Elizabeth to visit Portland Head Light, one of New England’s most iconic lighthouses.
This historic lighthouse sits on rocky bluffs in Fort Williams Park, offering a quintessential Maine coastal view (and lots of photo ops).
There’s an easy walking path along the shore and a small maritime museum in the former keeper’s house.
Next, continue up the Maine coast.
If you have time and interest in shopping, stop in Freeport, ME, home to L.L.Bean’s flagship store (open 24/7) and many outlet shops.
Otherwise, stay on US Route 1 which hugs the coast and passes through charming towns.
By late afternoon, make your way to the Midcoast area around Camden, Maine (about 1.5 hours from Portland).
Camden is a picturesque harbor town where the mountains meet the sea. Stroll Camden’s harbor park and watch classic schooners sail in and out of the bay.
You can drive or hike up to Camden Hills State Park’s Mt. Battie viewpoint for a panoramic look over Camden harbor and Penobscot Bay – it’s especially stunning at sunset.
Enjoy dinner in Camden or nearby Rockland – the seafood choices continue, or you might opt for Italian or farm-to-table fare with Maine ingredients.
Be sure to sample a blueberry pie or whoopie pie for dessert (Maine is famous for its wild blueberries!).
Overnight in the Camden/Rockland area, gearing up for tomorrow’s national park adventure.
Highlights:
- Portland Old Port – Shop and sightsee in this historic district. Fans of literature might stop at the Henry Wadsworth Longfellow House, and families could check out the hands-on Children’s Museum if needed as an indoor option.
- Portland Head Light – Walk around Maine’s oldest lighthouse (commissioned by George Washington!). Enjoy views of waves crashing on rocks and maybe a picnic in Fort Williams Park.
- Freeport (optional) – Visit the enormous L.L.Bean store (complete with a giant boot outside) – a Maine institution for outdoor gear and clothing.
- Camden, Maine – Soak in the New England coastal charm. In summer, you might catch an outdoor band concert at the Camden Amphitheatre; in cooler seasons, just enjoy the peaceful harbor scenery. Local tip: If time allows, a short walk to Barrett’s Cove on nearby Megunticook Lake shows a different side of Maine’s beauty (freshwater lake with a small beach).
Day 7: Acadia National Park, Maine – Peaks and Shores of Mount Desert Island
Drive about 2 hours further up the coast this morning to reach Acadia National Park on Mount Desert Island, Maine.
Acadia is the crown jewel of New England’s natural scenery – a national park offering mountains, forests, and dramatic ocean coastline all in one place.
Start at the Hull’s Cove Visitor Center to get park maps and info.
Then embark on the Park Loop Road, a 27-mile loop that links Acadia’s major sights.
Make sure to stop at Sand Beach, a beautiful crescent of sandy beach nestled between rocky shores (yes, a sand beach in Maine!).
From the Sand Beach parking, you can take the Ocean Path trail for an easy scenic walk along the rocky coast; it leads to Thunder Hole, a wave-carved inlet that creates a thunderous splash at high tide, and further to Otter Cliffs with sweeping ocean views.
Next, drive (or hike if feeling adventurous) up Cadillac Mountain, the tallest peak on the U.S. Atlantic coast (1,530 feet).
The summit road takes you to viewpoints where you can see vast panoramas of the Atlantic, forested islands, and the town of Bar Harbor below.
(Fun fact: at certain times of year, Cadillac’s summit is the first place in the U.S. to see the sunrise.)
In the afternoon, enjoy Jordan Pond – have a stroll on the Jordan Pond Trail for views of the Bubble Mountains reflected in the clear water.
You might also stop at Jordan Pond House to try their famous popovers with jam (a classic Acadia treat) if it’s open.
Acadia has 45 miles of carriage roads (gravel paths) built by John D. Rockefeller Jr., so consider a short walk or bike ride on one of these peaceful roads to see stone bridges and quiet forests.
As the day winds down, head into Bar Harbor, the main town on Mount Desert Island, for the evening.
Bar Harbor has a charming downtown with shops and restaurants. Indulge in a Maine lobster dinner – many restaurants offer whole steamed lobster or lobster bake meals (bib included!).
After dinner, you can walk Bar Harbor’s short Shore Path, which traces the coastline by the harbor for lovely twilight views.
Overnight in or near Bar Harbor.
Highlights:
- Park Loop Road (Acadia) – Drive this loop and stop often: in addition to Sand Beach and Thunder Hole, there’s Sieur de Monts Spring (with the Wild Gardens of Acadia) and Otter Point for more great views.
- Cadillac Mountain – Drive to the summit (road typically open spring through fall) for 360° vistas. Short paved paths at the top lead to different overlooks. Tip: Bring a jacket – it can be windy and cooler up there.
- Jordan Pond – An idyllic spot for photos. The 3.5-mile loop trail around the pond is mostly easy (boardwalk and dirt path) if you want a longer walk.
- Bar Harbor – Browse the gift shops for souvenirs like blueberry jam or local maple syrup. If traveling with kids, they might enjoy an evening ice cream cone from one of the many ice cream parlors on Main Street (try the blueberry ice cream!).
Day 8: Mid-Coast Maine to New Hampshire – Scenic Drive South
After soaking up Acadia’s beauty, it’s time to begin the journey southward.
If you’re an early riser, consider catching the sunrise from Cadillac Mountain before you depart – it’s an unforgettable experience as the sun lights up the sea and islands (just be sure to check if reservations are required for sunrise drive, seasonally they might be).
Depart Mount Desert Island and drive south on U.S. Route 1 along Maine’s coast.
This drive takes you back through Maine’s mid-coast region, so you can stop in any appealing seaside towns you missed on Day 6.
One popular stop is Wiscasset, ME, known as “the prettiest village in Maine.”
Here you can join the queue at Red’s Eats, a tiny red shack famous for one of Maine’s best lobster rolls – they pack a whole lobster’s worth of meat into each roll.
Even if you skip Red’s, Wiscasset’s Main Street has antique shops and a lovely waterfront to stretch your legs.
Farther south, another worthwhile detour is Kennebunkport, Maine, a quaint and upscale coastal town (about 1 hour south of Wiscasset, slightly off the main route).
In Kennebunkport, drive by Walker’s Point to see the former President Bush estate, browse the shops in Dock Square, or walk along Ocean Avenue for views of the rocky shore and mansions.
By mid to late afternoon, cross back into New Hampshire.
Make a stop in Portsmouth, NH, which you briefly passed on Day 6.
Portsmouth is a historic port city with a vibrant downtown.
If time allows, tour Strawbery Banke Museum, an outdoor history museum neighborhood with preserved houses dating from the 1600s through 1800s (demonstrations and costumed interpreters bring history to life here).
Even without a museum visit, Portsmouth’s Market Square and surrounding streets are fun to explore – you’ll find unique shops, colonial-era buildings, and maybe some street musicians.
Enjoy dinner in Portsmouth at one of the many restaurants (the city is known for its breweries and gastropubs as well as seafood).
Try some classic New England fare one last time – clam chowder, fish and chips, or hearty fisherman’s stew.
Overnight in Portsmouth or nearby, so you’re close to the Massachusetts border for the final leg tomorrow.
Highlights:
- Coastal Maine Drive – Meander down Route 1 and feel free to stop in towns like Belfast (arts and antiques), Rockland (check out the Farnsworth Art Museum if you love Wyeth paintings), or Damariscotta (known for its oysters), depending on your interests.
- Wiscasset, ME – Scenic small town. Aside from lobster rolls, don’t miss Treats bakery for coffee and pastries or the waterfront walkway behind Main Street.
- Kennebunkport, ME – Snap a photo at the Anchor by the Port landmark downtown or grab a treat at Rococo Ice Cream (creative flavors) if you need an afternoon pick-me-up.
- Portsmouth, NH – Charming brick architecture and rich history. If you have the evening free, you might take a Harbor Cruise or sunset sail from Portsmouth for one last look at the coastline from the water.
Day 9: Salem and Back to Boston, Massachusetts – Witches & Farewell
It’s the last full day of the road trip! From Portsmouth, drive just under an hour south to Salem, Massachusetts, a city famed for its 1692 witch trials history.
Salem offers a mix of fascinating history and New England charm.
Visit the Salem Witch Museum for an overview of the infamous witch trials (the presentation is engaging for a variety of ages, though younger children might find it a bit dark).
Afterward, explore Salem’s historic streets: Chestnut Street features grand old homes, and the Derby Wharf area highlights Salem’s past as a wealthy shipping port.
You can tour the House of the Seven Gables, a colonial mansion made famous by Nathaniel Hawthorne’s novel, or the Peabody Essex Museum, which has excellent art and history collections (including an authentic 200-year-old Chinese house rebuilt on site).
Salem’s downtown is fun to wander – you’ll find witch-themed souvenir shops and cafes in old brick buildings.
Grab lunch here (perhaps a cup of clam chowder or a lobster roll, if you haven’t had your fill!).
In the afternoon, make the final hop back to Boston (about 30 minutes to 1 hour drive, depending on traffic).
You’ll arrive in Boston where it all began, completing the loop through New England. If you have any unfinished sightseeing in Boston, now’s the time to do it.
You might cross the Charles River to Cambridge and walk through Harvard Yard, soaking up the collegiate atmosphere, or visit the Boston Public Garden to see the swan boats and “Make Way for Ducklings” statues that delight children.
For a grand finale, consider an evening harbor cruise or walk along the Charles River Esplanade at sunset to reflect on all the places you’ve visited.
Enjoy a final dinner in Boston – perhaps in the Seaport District with views of the skyline or back in the North End for a cozy Italian feast.
Overnight in Boston, ready for departure on Day 10.
Highlights:
- Salem, MA – Learn about the witch trials at museums or by visiting the historic sites (the Salem Witch Trials Memorial and Old Burying Point cemetery are in the center of town). In October, Salem’s Haunted Happenings festival brings an extra-spooky vibe, but any time of year the history is intriguing.
- House of the Seven Gables – Tour this seaside colonial mansion and its secret stairways. The gardens have great views of Salem Harbor.
- Harvard University (Cambridge) – Stroll the prestigious campus (free student-led tours are often available) and see Harvard Square’s bookstores and street performers. A fun stop for all ages is the Harvard Museum of Natural History, which has dinosaurs and the famous Glass Flowers exhibit.
- Boston Finale – Options abound: do some shopping on Newbury Street, take a serene walk in the Public Garden, or visit the Museum of Science if you have kids and a few hours to spare. Don’t forget to pick up any souvenirs (maybe a bag of saltwater taffy or a Harvard T-shirt) to commemorate your New England adventure!
Day 10: Departure from Boston – Goodbye New England
Your New England road trip comes to an end today.
If you have a bit of time in the morning before departing, enjoy a relaxed breakfast at a local café – perhaps indulge in blueberry pancakes or a Boston cream doughnut.
Depending on your schedule, you could do a last-minute stroll along the Harborwalk by Boston Harbor or revisit a favorite spot from Day 1.
Then, make your way to Boston Logan Airport (or your chosen departure point) to drop off your car and head home.
Congratulations!
And that’s it!
In 10 days, you’ve experienced a rich variety of New England’s offerings!
From historic cities and coastal villages to mountains and national parks, you’ve covered hundreds of miles and countless years of history.
This itinerary packed in a lot, but each stop was chosen to give you a genuine taste of New England’s charm, culture, and natural beauty.
We hope this journey leaves you with wonderful memories and maybe a desire to return because there’s always more to discover in New England.
Safe travels home!
Trip Wrap-Up Tips
Tolls and Traffic
New England has some toll roads (e.g., Massachusetts Turnpike, Maine Turnpike).
Consider getting an EZ-Pass transponder or be prepared with cash/credit for toll booths.
Also, plan for possible traffic congestion near cities (Boston in particular) – try to time your driving outside of rush hours.
Weather Ready
New England weather can change quickly.
Pack layers and a light rain jacket so you’re comfortable exploring cities or hiking trails, rain or shine.
Flexibility
Use this itinerary as a guide, but feel free to adjust based on your interests.
New England has many hidden gems; if a local recommends a great little museum or a beautiful back road, go for it!
The best road trips leave room for spontaneous discoveries.
Enjoy your New England adventure!
