Book Now
The view of Frenchman Bay from Bar Harbor
Back

A Coveted Coastal New England Road Trip

The beauty of a multi-day, 220-mile road trip up the craggy coast from Portsmouth, New Hampshire to Bar Harbor, Maine isn’t just the plethora of enticing pit stops along the route – from high culture to scenic coves. It’s also the way that Opal properties serve as your easy and convenient overnight waypoints for piecing together one epic coastal cruise.


Ever been on a stretch of road where it feels like the pavement plods on for miles without a stop-worthy roadside attraction in sight? If the answer is yes, then you definitely weren’t in coastal New England. Because here, the pressure to pull over is ever-prevalent thanks to easily accessible roadside stops: Everything from scenic coves studded with bobbing boats to quaint lobster shacks and antique emporiums to stretches of downtowns lined in retailers, restaurants, and museums.

So how do you fit it all in without turning your trip into what could stretch into a month-long journey? You follow this carefully crafted itinerary, culling the top New England road trip stops, starting from Portsmouth, New Hampshire to Portland, Maine, then onto Rockport and ending in Bar Harbor.

LEG 1: PORTSMOUTH, NH TO ROCKPORT, ME | 136 MILES

Depart from Wentworth by the Sea [Portsmouth, NH]

After waking up in one of the cozy seaside rooms of Wentworth by the Sea – located just 15 minutes from downtown Portsmouth on the island of New Castle – make sure to fuel up for your ride with breakfast from the 1874 grand hotel’s on-site signature restaurant, Salt Kitchen & Bar. Dishes include from-the-griddle favorites like buttermilk pancakes as well as coastal twists on classic egg creations, from the lobster benedict to smoked salmon avocado toast.

Visit One of the Many Museums in Maine’s Largest City [Portland, ME]

The view of Portland, Maine's skyline.

After a little over an hour on I-95 North, you’ll make your first stop in Portland where a rich port history blends with high culture, making it one of the hippest, vibrant small cities in America. It’s also something of a museum mecca, offering everything from the prestigious Portland Museum of Art, home to coveted masterpieces from the likes of Claude Monet, Winslow Homer, and Pablo Picasso, to the weird and whacky wonders of the International Cryptozoology Museum or the Umbrella Cover Museum.

Take Scenic Route 1 for a Lobster Lunch at Red’s Eats [Wiscasset, ME]

A classic Maine lobster roll.

Instead of remaining on I-95, opt to take oceanfront Route 1 for its classic Maine coastal views. Time it just right, and you should hit the historic and quaint village of Wiscasset for a late lunch, where a postcard perfect red-and-white striped lobster shack – known as Red’s Eats – waits with first-rate lobster rolls along the Sheepscot River. If looking for a nearby alternative that also remains open in the off-season (as Red’s season runs from April to October), check out  Water Street Kitchen just down the road for a unique Mediterranean spin on Maine seafood.

Check into Samoset Resort then Depart for Downtown [Rockport/Rockland, ME]

Two woman shop in downtown Rockland.

After about a 45-minute ride from Wiscasset, it’s check-in time at Samoset Resort, a nautically inspired property set on 230 acres overlooking Penobscot Bay’s deep-water harbor in Rockport. But you’re not calling it a night just yet: After getting settled, set out for exploring downtown Rockland, located just a 10-minute drive from Samoset and considered one of Midcoast Maine’s most charming towns where historic brick buildings take on second lives as cutting-edge restaurants, hip and lively coffee shops, upscale boutiques, and eye-opening art galleries. We suggest beelining it to Main Street, the village’s bustling nerve center, home to such institutions as the Strand Theatre, The Grasshopper Shop, and the nationally recognized Farnsworth Art Museum.

Italian Eats at Samoset Resort [Rockport, ME]

The Italian-inspired dishes at La Bella Vita.

After working up an appetite strolling the streets of downtown Rockland, you’ll be more than ready to dig into dinner at Samoset’s signature on-site restaurant, La Bella Vita. Styled with a rustic charm that captures the ambiance of a traditional trattoria, the eatery presents classic Italian dishes done up with Maine ingredients, like the lobster and crab ravioli and Sicilian ocean stew. After pouring over the menu of pastas, pizza, seafood, and more, don’t forget to peek the extensive wine list – which earned a Wine Spectator “Award of Excellence” in 2022 – for the perfect pairing.

The 2024 Bar Harbor Season is Here!

After a lovely winter’s nap, we’re excited to announce that our Bar Harbor Opals – Harborside Hotel, Spa & Marina and West Street Hotel – are open and welcoming guests! We can’t wait to see you!
Book Your Maine Getaway Today

LEG 2: ROCKPORT, ME TO BAR HARBOR, ME | 85 MILES

Depart from Samoset Resort, But Not Before Doing Breakfast & Breakwater [Rockport, ME]

The Rockland Breakwater in Rockport, Maine.

Before departing from the seaside elegance of your room, make sure to take full advantage of the resort’s lengthy in-room dining menu, whisking everything from buttermilk pancakes to egg white omelets to your bedside or balcony. After checking out, it’s time for one last on-resort adventure: The Rockland Breakwater. Located at the edge of the property, this marvel of a jetty constructed from massive blocks of granite juts out into the bay for almost a mile. It takes about 15 minutes to stroll the full length (round trip) of the landmark, where on its easternmost end, a lighthouse stands sentinel over the harbor.

Visit a Maine Vineyard [Lincolnville, ME]

The view from the vineyard at Cellardoor Winery.
© Emily Qualey, courtesy of Celldardoor Winery

After departing Rockport, take a quick pit stop to nearby Lincolnville, Maine, just 15 minutes north and home to Cellardoor Winery. This establishment not only showcases its state-of-the-art winery but is also home to a 5.5-acre vineyard and large barn for sampling their 20 wines made largely from imported grapes (with the exception of their ice wine). Tours of the winery are offered at 11:30 a.m. on Saturdays and Sundays, and self-guided tastings are available from 12 to 5 p.m. Friday through Sunday. For a more intimate and educational experience, hosted tasting bars are available by reservation on Saturday and Sunday afternoons with a Cellardoor host.

Stop at the Penobscot Narrows Bridge & Observatory [Bucksport, ME]

The view of the Penobscot Narrows Bridge from the Penobscot River.
© Adam Grotton

After grabbing lunch at one of the many roadside stops that line Route 1 from Belfast to Stockton Springs, stop at the first (and tallest) bridge observatory in the world, the Penobscot Narrows Bridge and Observatory. Connecting Verona Island to Prospect, Maine, the 446-foot-tall structure towers over the Penobscot River with a public observatory offering 360-degree views extending to Mt. Desert Island and Acadia on a clear day.

Check into West Street Hotel Then Sail into Sunset [Bar Harbor, ME]

A couple walks to board a catamaran with the Bar Harbor Whale Watch Company.

While Bar Harbor is home to two Opals – Harborside Hotel, Spa & Marina and West Street Hotel  –  tonight, you’ll be resting your head at the latter and the only luxury boutique hotel in town, featuring modern design, magnificent ocean views, and one truly breathtaking rooftop pool. After enjoying the ocean breeze from your private balcony as you look out to the yachts and fishing boats moored side by side at the marina, venture on a sunset cruise with Bar Harbor Whale Watch Company. Highlights include cruising through the evergreen tree-topped islands of Frenchman Bay, sipping a local brew, and, of course, soaking up that technicolor sunset.

A Hearty Dinner to Fuel Your Following Day [Bar Harbor, ME]

Paddy's, located on the street level of West Street Hotel, in the evening.

The major road trip portion of your trip may be done, but you’re just getting started in Bar Harbor. And for that reason, you’ll want a hearty meal to fuel your day ahead. Luckily, you have your choice of diverse dining in downtown harbor, but we recommend either Paddy’s Irish Pub, located on the street level of the West Street Hotel, or Stewman’s Lobster Pound. (Can’t decide? Check out our guide to both). Over dinner, plot out your following day spent exploring the jagged granite peaks, rugged coastline, and historic carriage roads of Acadia National Park just a few miles away. In fact, a great way to take it all in is via one of the island’s new Acadia GEMs, clean energy efficient, lightweight electric vehicles that are street legal and available for rental in the heart of Bar Harbor. Think of it as a way to extend your road trip just a little while longer.

OTHER ROAD TRIP-THEMED ARTICLES ACROSS OUR OPALS

You may also like

Lake George or Lake Placid? Your Ultimate Comparative Guide

If you were to ask a native New Yorker about the best Adirondack vacation destinations, the locations of “Lake George” and “Lake Placid” are usually said in the same breath. But that certainly doesn’t mean they are exact carbon copies…

Read more
A burger at the new BRGR Bar & Kitchen.

Bring on the Burgers: BRGR Kitchen & Bar Comes to Bolton Landing

You heard correctly: Mr. Brown’s Pub – a longtime staple of the dining outlets at The Sagamore Resort – has transitioned to become a gourmet burger restaurant. For the devout fans of Brown’s, though: Don’t fret. It still features the…

Read more

Mining from the Menus: A Delicious Tribute to Wentworth’s 150 Years

Wentworth by the Sea, a Grand Dame Hotel perched on a seaside bluff in New Castle, officially turns 150 years old in June of 2024. In addition to paying tribute to the landmark birthday with special historically-themed programming, the hotel…

Read more
A couple strolls along the Bar Harbor Shore Path.

7 Fun Facts About Maine You Never Knew

Maine is the first state that sees sunlight every day…but did you know that the precise locations change throughout the year? How about despite there being thousands of coastal islands, only a handful are inhabited year-round? Or that while lobster…

Read more