New England Mountains & Cape Cod Road Trip

There’s no better place to begin your road trip than Boston. The city is one of the nation’s oldest and you’ll spend a few days exploring its many museums and monuments.

As well as enjoying an organised guided history tour, you’ll have a chance to admire 16 different heritage sites — including Old State House and Paul Revere House — on the 2.5 kilometre long Freedom Trail. Boston is also known for its green spaces. Enjoy a picnic on pretty Boston Common or head into the Blue Hills Reservation to soak up panoramic skyline views.

Boston’s Seaport District is a brilliant place to sample local cuisine, including Boston clam chowder. Alternatively, you’ll find a wide selection of gourmet dining spots in the historic Faneuil Hall Marketplace.

Cross over the state border into Maine to explore Portland. The coastal city has a long seafaring heritage, and its historic Old Port is a must-see for any first-time visitor. The cobblestone docks are lined with 19th-century warehouses that host a mix of restaurants, bars and boutique shops.

Portland Arts District is essential viewing for those who love spending afternoons wandering around galleries. During your visit, you’ll also have the chance to embark on a guided trolley tour where you’ll visit key city sites such as the 19th-century Victoria Mansion.

Want to sample local cuisine? Portland has regular farmer’s markets where you can purchase delicious artisanal products. There are additionally several breweries and cideries on the outskirts of the city which offer tasting tours. For fantastic viewpoints, put the Portland Observatory on your itinerary or stroll along one of the coastal paths leading to Portland Head Light — the oldest lighthouse in the state.

Continue your journey through Maine to Bar Harbor, a bustling summer destination about three and a half hours from Portland. The town sits on Mount Desert Island and is a gateway to the spectacular Acadia National Park — a hub for all kinds of outdoor activities.

Look forward to rock climbing, kayaking, sailing and hiking adventures which let you soak up the region’s extraordinary natural beauty. If you’re an early riser, you might want to make the scenic three-mile drive to the summit of Cadillac Mountain to watch the sun rise over the ocean. There’s also the Shore Path in the town where you can enjoy uninterrupted views of the nearby Porcupine Islands.

Bar Harbor was once a retreat for the rich and famous, so you’ll discover a handful of elegant mansions and museums open for tours. Other potential excursions include whale-watching expeditions and cross-country skiing (winter only). After an active day out, you can unwind in one of the many trendy restaurants and bars along Bar Harbor’s attractive waterfront.

Next up on your agenda is North Conway, a scenic four-and-a-half-hour drive away in the White Mountains. The region makes up almost a quarter of New Hampshire and it’s crisscrossed with wonderful walking routes, including a section of the historic Appalachian Trail.

You’ll likely want to relax after your journey, so make a beeline for the town’s pretty centre where you’ll find local dining spots and charming craft shops. North Conway is a brilliant base for all kinds of outdoor pursuits, from rock climbing in the mountains to canoeing and fishing in various nearby lakes.

Swap the White Mountains of New Hampshire for Vermont’s equally picturesque Green Mountains. You’ll stay in Stowe — the so-called ‘Ski Capital of the East’. If your road trip falls during the winter or early spring, you’ll have several snow sports to enjoy, from cross-country skiing and backcountry snowshoeing to dog-sledding and sleigh rides.

Stowe is a quintessential mountain town with no shortage of charming attractions. Spend an afternoon hopping between antique shops and art galleries along Main Street. You could also stroll across the 19th-century Gold Brook Covered Bridge or visit the Trapp Family Lodge: a resort founded by the same family that inspired The Sound of Music.

Stowe has an abundance of cosy inns, inviting restaurants and craft breweries. The region is also famed for its maple syrup and you’ll be able to sample it during themed farm tours. Prefer ice cream? Add the Ben and Jerry’s Ice Cream Factory in nearby Waterbury to your bucket list.

Continue your road trip by heading south to Manchester. The former mining town is also nestled in the Green Mountains and it’s a brilliant destination for fly fishing, snow tubing, hiking and golfing.

Spend some time exploring the town on your own. Begin at the Manchester Village Historic District where you’ll uncover fascinating heritage sites such as Hildene (Abraham Lincoln’s son’s former home) and the Equinox Village Shops with their pretty 18th-century storefronts.

The town is also a major creative hub. Browse the exhibits at the Southern Vermont Arts Center or book tickets to an off-Broadway show at one of Manchester’s theatres.

The next stop on your road trip is Stockbridge, Massachusetts, set amid the breathtaking Berkshire Mountains.

You’ll have a couple of days to explore Stockbridge and the surrounding area at your own pace. Soak up the scenery by hiking to view points or tackling the region’s rugged cycling trails. Stockbridge is also known for being the former home of painter Normal Rockwell and sculptor Daniel Chester French. Visit the Norman Rockwell Museum to look at hundreds of his paintings or tour Chesterwood, Chester French’s estate that now has National Historic Landmark status.

Other notable attractions include the 18th-century Red Lion Inn which famously hosted an array of former presidents and celebrities. You could also go back in time with a tour of the Federal-style Merwin House or the brilliant 18th-century Bidwell House Museum.

Rhode Island is your next port of call. You’ll stay in Newport, a buzzing seaside city on Aquidneck Island that’s well-known for its elegant Gilded Age mansions. During your visit, you’ll have the chance to learn more about them on a trolley tour that takes you down Newport’s most historic streets.

You will also have time to wander the city’s National Historic District at your leisure and pop into various grand estates filled with priceless artefacts. Prefer automobiles to antiques? Don’t skip visiting the Newport Car Museum which explores eight decades of automotive design.

Newport’s Cliff Walk is a must-do, with the route taking you past numerous coastal mansions. There is also the Fort Adams State Park that’s perfect for a picnic, in addition to several wineries and breweries where you can enjoy tasting tours.

Journey two hours to the penultimate stop on your trip: Hyannis. The picturesque town sits on the Cape Cod Peninsula and you’ll have the opportunity to glimpse magnificent marine life off its dazzling shores.

Walk barefoot along the sand at Kalmus or Craigville Beach before sampling local seafood, including fresh lobster, at a waterfront restaurant. You could also sail around Hyannis’s natural harbour or set off on day trips to nearby islands including Nantucket and Martha’s Vineyard. As part of your itinerary, you’ll have the chance to join a Hyannis Whale Watcher Cruise around Cape Cod’s Stellwagen Bank National Marine Sanctuary.

Hyannis also packs a punch with its culinary and cultural offerings. Peruse the town’s art galleries before dining on New England delights on Main Street. You’ll also want to follow the Kennedy Legacy Trail which takes you past a handful of heritage sites linked to the Kennedy family, including the John F Kennedy Museum.

Wave goodbye to Cape Cod as you return to Boston for a final day of sightseeing. Tick off any attractions you missed or spend time relaxing. You could always catch a baseball game at Fenway Park or gaze at glorious artworks at one of several city galleries.

Once night falls, you’ll join a guided ghost tour of Boston’s most storied sites. What better way to round off your trip than with a few fascinating — and sometimes spooky — tales of the city’s past?