Set off on an epic journey from one historic USA city to another with our Little Gems and Secrets of the Northeast Road Trip.
The 23-day itinerary is packed with towns and cities known for their distinct cultural allures, elegant architecture and stunning natural surroundings.
You’ll begin your journey in Boston — a city steeped in history. Explore it on foot as you walk along various dedicated trails. Don’t forget to sample some authentic Boston clam chowder. Next up on your agenda is Rockport, a Massachusetts city famed for its arts and crafts scene.
Move on to picture-perfect Portland where you’ll enjoy a blend of gallery visits, brewery tours and alfresco harbourside dining. Boothbay Harbor, just 90 minutes east, is your next stop and a haven for wildlife tours and beautiful hikes to historic lighthouses.
The middle section of your road trip will take you into the dramatic White Mountains. Split your time between two towns, North Conway and Franconia, and enjoy daily hiking, biking and some skiing excursions. Continue to Manchester in the nearby Green Mountains to explore its Historic District and enjoy off-Broadway shows at its collection of theatres.
The Finger Lakes is your next port of call. Use Ithaca as your base and embark on trips to scenic state parks sprinkled with waterfalls and walking trails. You’ll then hop over the Canadian border for a few days to see one of the most famous waterfalls in the world: Niagara Falls.
After a brief interlude in historic Gettysburg to admire its Civil War monuments, you’ll end your road trip in Washington D.C. Tick off some of the US capital’s key attractions, including major museums and iconic political buildings.
Whether you love history, food or nature, this itinerary has universal appeal. It’s also the perfect match for those who want to sample the culinary delights of the Northeast or enjoy once-in-a-lifetime experiences in this part of the country.

Trip Highlights
- Follow city centre walking trails lined with historic monuments or cruise along the Charles River in Boston
- Enjoy the great outdoors in the White Mountains
- Lose yourself for a few hours in the art galleries and craft shops of Portland and Rockport
- Admire one of North America’s most iconic natural sights up close at the tumbling Niagara Falls
- Venture to Washington D.C. and immerse yourself in United States history and politics at various landmarks
Start your Journey
Boston, MA
You’ll start your road trip with a couple of days in bustling Boston, Massachusetts. Stroll past a string of heritage sites along the 2.5-kilometre Freedom Trail or venture to the Seaport District to visit the Boston Tea Party Ships & Museum.
Take in spectacular views of the Boston skyline from the Blue Hills Reservations. Hike through the hills before returning to the city’s waterfront for a bowl of Boston clam chowder. You could also spend an afternoon relaxing at pretty Boston Common followed by a sunset cruise on the city’s famous Charles River.
Rockport, MA
Say goodbye to Boston as you hop in your hired car and drive one hour to Rockport. The Massachusetts city is equally as historic and well-known for its artistic connections. Spend a day exploring art galleries and perusing the craft boutiques along the Bearskin Neck peninsula.
Enchanting woodlands and beautiful beaches abound in Rockport. You’ll also have the chance to admire ‘Motif No.1’; a striking red fishing shack in the harbour that’s long been a source of inspiration for budding painters. No trip to Rockport is complete without tucking into some local wine and cuisine. You’ll find plenty of restaurants serving fresh seafood along the waterfront.
Portland, ME
Continue your journey with a breezy two-hour drive to Portland in the neighbouring state of Maine. The city has a distinctive seafaring heritage and a great culinary scene. Portland’s Arts District is home to brilliant galleries such as the Portland Museum of Art, while the 19th-century warehouses in the Old Port house all manner of restaurants and independent boutiques. Foodies can also visit the city’s Farmer’s Market to sample artisan treats or sip craft beer during a tour of the Allagash Brewing Company building.
Step back in time during a guided trolley tour of Portland which takes you past the opulent, Italian-style Victoria Mansion. If you fancy a walk afterwards, you’ll discover miles of splendid coastal paths around Portland Head Light — Maine’s oldest lighthouse. You can also enjoy great views from the Portland Observatory or during the short ferry ride to the nearby Casco Bay Islands.
Boothbay Harbor, ME
Maine’s Boothbay Harbour is your next stop. Head down to the bustling harbourfront to discover why Boothbay is known as the ‘Boating Capital of New England’.
You’ll also have plenty of opportunities for leisurely walks to scenic coves and historic lighthouses. If the weather’s good, join a boat excursion to Burnt Island or Monhegan Island to spot seals, puffins and even whales. History lovers will love the antique locomotives at the century-old Boothbay Railway Village. Boothbay is known for its fresh seafood and you could stop for delicious meals at some of its top dockside restaurants.
North Conway, NH
Move onto North Conway, a scenic three-hour drive away in the White Mountains. The rugged peaks take up nearly a quarter of New Hampshire and this is where you’ll find the breathtaking Appalachian Trail.
You’ll have a chance to enjoy all kinds of outdoor pursuits such as walking and cycling in North Conway. It’s also possible to soak up the landscape during an off-road driving tour or via an old-fashioned cog railway. The White Mountains have several serene lakes where you can swim, canoe or fish.
Back in North Conway, you’ll have a choice of cosy local restaurants to dine at during the evenings.
Franconia, NH
Enjoy a couple more days in the White Mountains with a stay in Franconia, just 90 minutes west of North Conway. Explore the leafy trails in Franconia Notch State Park, including those that weave their way to the summit of Mount Lafayette.
Visiting in winter or early spring? The area is a major snow sports hub. Check out the runs at Cannon Mountain Ski Resort or learn all about the region’s skiing history at the New England Ski Museum.
Manchester, VT
Continue your journey to Manchester. The former mining town is tucked away between the Green Mountains and Taconic Mountain Range.
You’ll have plenty of time to discover Manchester at your leisure. Start with a stroll around the Manchester Village Historic District where you’ll spot landmarks such as Hildene: the former home of Abraham Lincoln’s eldest son, Robert. Manchester is also home to several world-class golf courses and a popular spot for fly fishing.
If you want to try out snow tubing or dog sledding, the surrounding mountains — including Mount Equinox and Mount Bromley — are winter sports playgrounds. Prefer to stick to the town? Manchester is blessed with a wonderful creative scene. Catch an off-Broadway show at one of its theatres or peruse the eye-catching exhibits at the Southern Vermont Arts Center.
Ithaca, NY
Next up, you’ll discover the Finger Lakes region in neighbouring New York state. Use the town of Ithaca as your base and enjoy self-guided trips to stunning state parks, enchanting waterfalls and wonderful walking trails.
The 11 narrow bodies of water that make up the Finger Lakes are a paradise for boating and fishing adventures. Wine connoisseurs will also be able to sip the lush region’s crisp Rieslings at numerous vineyards along the Seneca Wine Trail. There are cideries and breweries offering tours too, while those keen to shop will love exploring the vintage stores on Ithaca's charming streets.
The area is famed for its car racing credentials, too. You could check the calendar to see if any events are being hosted at the Watkins Glen International racetrack or fly around the track yourself during a guided tour.
Niagara Falls, ON
On day 16 of your road trip, you’ll cross over the border into Canada to view one of North America’s most stunning spectacles: Niagara Falls. You’ll be based in bustling Niagara Falls City and have a variety of activities to add to your agenda.
Made up of three tumbling cascades — American, Canadian Horseshoe and Bridal Veil — Niagara Falls is a bucket list attraction. Admire it during an organised group excursion which takes you through Niagara Gorge through the Hornblower Niagara Funicular before sailing close to the bottom of the falls on a state-of-the-art catamaran. Alternatively, view the falls during a private helicopter ride or on a self-guided hike.
The local area comes alive with beautiful botanical gardens and countless trails which you can traverse on foot, bicycle or horseback. Niagara Falls is also a short drive from several historic battlefields, in addition to rolling vineyards and manicured golf courses.
Gettysburg, PA
Today, you’ll swap outdoor treasures for historic gems when you journey back across the border to Gettysburg. The sleepy Pennsylvania town lies on the banks of Rock Creek and is best known as the location where Abraham Lincoln delivered the Gettysburg Address in November 1863.
Gettysburg’s historic downtown is packed with striking pre-Civil War buildings (including the grand Gettysburg Hotel) and intriguing museums. You’ll have the chance to tour American Civil War battlefields and uncover the town’s links to the Civil Rights Movement. Gettysburg is also a fantastic destination for foodies. Look forward to dining at farm-to-table restaurants and visiting the stalls at local farmer’s markets.
The countryside around Gettysburg offers up lots of activity options, too. You could explore local orchards on horseback, tour a winery or stroll the picturesque grounds of the quaint Eisenhower farm: the former home of President Dwight Eisenhower.
Washington D.C.
You’ll spend the final days of your trip in the US capital. Journey two hours from Gettysburg to Washington D.C. and drop off your car at the airport before heading into the city.
As well as enjoying a guided tour of Washington D.C. (including VIP entry to the domed US Capitol building), you’ll have time to see several other attractions at your own pace. The city’s streets are filled with world-class museums and iconic monuments, from the White House and Capitol Hill to the Smithsonian Centre. Other unmissable sites include the Lincoln Memorial, the National Archives and the Washington Monument.
You’ll additionally be able to embark on a leisurely cruise along the Potomac River or enjoy concerts and annual arts festivals at various open-air venues. Washington D.C.'s diverse range of neighbourhoods offer up a melting pot of dining and drinking options, from Michelin-star restaurants and rooftop bars to sensational street food venues.
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