New England Road Trip: 5-Day Itinerary

Google Map link (one-way Boston/Bangor)

Google Map link (round trip Boston)

From Boston’s historic streets to New Hampshire’s scenic byways and Maine’s rugged coastline, this five-day New England road trip captures the region at its most beautiful. The journey begins in the White Mountains, then continues east to Acadia National Park, blending mountain scenery, coastal beauty, and worthwhile stops along the way. In autumn, it feels especially magical, when fall foliage lights up the forested slopes and rocky shorelines in brilliant color. With both mountain and coastal landscapes in one itinerary, this is arguably one of New England’s most rewarding road trips.

Here’s your guide to planning the perfect five-day New England road trip.

About the 5-Day New England Road Trip

There are two ways to approach this road trip. For the most efficient route, fly into Boston Logan International Airport (BOS) in Massachusetts, where you can easily rent a car, then fly out of Bangor International Airport (BGR) in Maine to make the most of your time and avoid backtracking. However, if you want to enjoy more of the coast and have time to spare, a round-trip route to and from Boston also works very well.

With two nights at Under Canvas White Mountains and three nights at Under Canvas Acadia, this fast-paced five-day itinerary balances scenic drives, East Coast charm, mountain views, and coastal access, making for a memorable New England road trip.

5-Day New England Road Trip Snapshot

Total distance: 550 miles (one-way) or 840 miles (round-trip)

Start/end point: Boston, Massachusetts/Bangor, Maine or a round-trip from Boston

Best time to go: Late spring through early fall (May through October)

Day 1: Start in Boston, Drive the Kancamagus Highway, & Arrive in the White Mountains

Drive time: 3.5 hours | Distance: 200 miles

Fly into Boston, pick up a rental car, and head north toward New Hampshire’s White Mountains. While the drive takes only about 2.5 hours to complete, it’s worth leaving room for a few quick stops along the way. You might pause for a few sights along Boston’s Freedom Trail, make a brief detour to Salem for dark history, or stop in Concord to stretch your legs, grab a coffee, and admire the gold-domed State House. Keep these stops light, though. The main event is the drive through the White Mountains, especially the Kancamagus Highway.

The Kancamagus Highway (NH Route 112) branches off from your route north and is one of New England’s most scenic drives. This 34.5-mile byway runs between Lincoln and Conway through the White Mountain National Forest, with sweeping views, forested slopes, and scenic pullouts along the way. Drive it east from Lincoln to Conway, then turn around and return the same way to take it in from a different perspective. Experiencing the Kanc in both directions makes it a true highlight of your first day in the White Mountains.

Continue north for 45 minutes to Under Canvas White Mountains, where you can settle into your safari-inspired glamping accommodations for comfort in nature, surrounded by rolling meadows, orchards, and views of the Presidential Range.

Day 2: Explore the White Mountains: Franconia Notch, Flume Gorge, & Scenic Railways

Drive time: 2 hours | Distance: 85 miles

Spend the day exploring the White Mountains. Start in nearby Franconia Notch State Park, one of New Hampshire’s most spectacular mountain corridors. One of the park’s signature attractions is Flume Gorge, a natural granite chasm at the base of Mount Liberty where boardwalks lead past towering rock walls, rushing water, covered bridges, and mossy forest, for a memorable 2.2-mile hike.

Pro tip: Make a reservation in advance, as walk-up availability is not guaranteed.

Later, choose one of two classic rail experiences. For a more dramatic adventure, ride the Mount Washington Cog Railway, which climbs toward the highest peak in the Northeast for big mountain scenery and summit views. For something slower and more romantic, choose the Café Lafayette Dinner Train in North Woodstock (not far from Flume Gorge). This experience is less about elevation and panoramic vistas and more about atmosphere: a relaxed two-hour ride aboard vintage rail cars through the Pemi River Valley paired with a five-course meal.

By evening, return to Under Canvas White Mountains for one more night of upscale glamping, where you can unwind by the fire with s’mores and a sky full of stars overhead.

Day 3: Drive from the White Mountains to Acadia

Drive time: 4.5 hours | Distance: 220 miles

Start early and enjoy the changing scenery as you leave New Hampshire behind and make your way toward Maine.

A great first stop is Bethel, a classic New England town with a walkable downtown that is ideal for coffee or lunch. If you want to stretch your legs a bit more, you can also visit the Maine Mineral & Gem Museum or stop by the picturesque Sunday River Bridge (Artist’s Covered Bridge) in nearby Newry.

For a bit more history, head to Fort Knox and the Penobscot Narrows Observatory, where one of the best-preserved forts in New England is paired with sweeping river views. For a coastal-town stop, stop in Belfast instead, where the waterfront and historic downtown offer a charming introduction to Maine’s coast.

Check in at Under Canvas Acadia, set on 100 acres of waterfront property near Acadia National Park. After a long but scenic travel day, it’s the perfect place to refresh and unwind. Settle into your safari-inspired tent, relax on your private deck, and take in the fresh air and water views before your park adventures begin.

Day 4: Explore Acadia National Park: Cadillac Mountain, Park Loop Road, & Bar Harbor

Drive time: 4 hours | Distance: 70 miles

Start early for sunrise at Cadillac Mountain, one of Acadia’s must-do experiences. From the summit, you’ll take in sweeping views over the Porcupine Islands and Frenchman Bay. Reservations are required to drive Cadillac Summit Road from mid-May through mid-October from sunrise to sunset. You can visit without a vehicle reservation by arriving before sunrise, hiking the 2.2-mile one-way North Ridge Trail, or biking to the top.

Continue onto Acadia’s Park Loop Road, the park’s scenic 27-mile driving route that links many of its iconic sights. For a classic coastal stop, pull over at Sand Beach for a swim and walk part of Ocean Path, a scenic shoreline trail that runs toward Otter Point. Stop at overlooks like Thunder Hole and Otter Cliff as you make your way around the loop.

Pro tip: The best time to check out Thunder Hole is 1–2 hours before high tide, when the splashes and thunderous booms are at their peak.

Pack a picnic lunch from Under Canvas Acadia to enjoy by the shore. Food options inside Acadia National Park are limited unless you leave the park for Bar Harbor, so bringing lunch will help you make the most of your time.

When you’re ready to leave the park, head to Bar Harbor for a dose of small-town coastal charm, whether that means a waterfront stroll or browsing the shops for a souvenir before returning to camp.

By late afternoon or evening, settle back in at Under Canvas Acadia for live acoustic music, fresh Maine seafood, and s’mores around the campfire beneath the stars.

Day 5: Explore Acadia National Park: Jordan Pond, Carriage Roads, & Sunset Cruise

Drive time: 2 hours | Distance: 45 miles

Start at Jordan Pond, one of the park’s most photographed spots, reached from the Park Loop Road. Enjoy a famous popover on the lawn of the historic Jordan Pond House with stunning views. Reservations recommended.

After lunch, you can choose to hike the easy 3.5-mile round-trip Jordan Pond Loop Trail around the entire pond to admire the surrounding hills known as “The Bubbles.”

From there, continue onto Acadia’s historic carriage roads, a 45-mile network of motor-free roads that weave through mountains, forests, and lakes. Whether you choose to bike or walk a scenic stretch, this part of Acadia offers a completely different feel from the coastal overlooks of the day before.

Round out the day with a sunset cruise on Acadia’s waters, where breathtaking coastal views, local history, and the chance to release a wish lantern make for a memorable evening. Enjoy fresh lobster rolls as the sun dips toward the horizon, then return to Under Canvas Acadia for one last night of glamping.

The next morning, begin the drive to Bangor International Airport (BGR), just 35 miles (45 minutes) from Under Canvas Acadia, to return home.

Tips for a New England Road Trip

• America the Beautiful Pass: If you visit multiple national parks in a year, the annual pass quickly pays for itself.
• Park Day Essentials: Pack snacks, plenty of water, sturdy shoes, and sun protection to stay comfortable.
• Timed Entry Requirements: Check the National Park Service website for reservation, timed-entry, and permit requirements.
• Fuel & Cell Service: Fill up when you can, and download offline maps if cell service is limited.
• Stay & Save: Staying at two or more Under Canvas camps gets you 20% off your multi-camp stay. Contact the reservations team at 888-496-1148 or reservations@undercanvas.com.

Where to Stay on a New England Road Trip

Immerse yourself in the great outdoors with upscale, safari-inspired glamping at Under Canvas camps in New England. Each camp blends comfort and adventure through thoughtfully designed canvas tents, upscale amenities, optional en suite bathrooms, cozy king-size beds, dining, and campfire traditions. Enjoy daily camp programming for all ages, nightly s’mores, and adventures for an unparalleled experience in nature.

BOOK YOUR STAY

Explore our 7-day New England road trip itinerary to experience even more.