On the hunt for an adventure, my Travel Curator colleague Roberto and I set out on a road trip to explore New England. Our mission? To immerse ourselves in quintessential New England charm, visit quaint boutique hotels and search for the best lighthouses, lobster rolls, and scenic beauty. Along for the ride was ‘Droney’ TC’s resident cameraman who dutifully shot some stunning aerial footage of the coastline, sweeping bluffs, and our nature-filled drive from NYC through Connecticut, Rhode Island, New Hampshire, and Maine (where those lobsters were waiting).
Day 1: NYC ➝ Connecticut ➝ Rhode Island
Drive Time: 3hrs, 50 mins
After a bumpy start at Hertz to pick up our rental car (long story, don’t ask) we left New York for Providence on the first leg of our six-day road trip. The drive from the city taking us through the countryside to Essex, where we stopped for our first taste of New England fare at a landmark pub and inn.
Lunch: The Griswold Inn (Essex, CT)
The cozy, charming Griswold Inn, a tap house, restaurant, and inn in the seaport village of Essex, CT is a little slice of marine history that dates back to 1776. The walls are lined with sea-faring photos and memorabilia from days gone by and the Americana menu, executive chef Toppin focuses heavily on fresh New England seafood and aged beef. We both went for the clam chowder followed by sea scallops (Rob) and fish and chips (me) washed down with a local draft beer to the sounds of live music. We sat inside in awe of the historic, almost maritime museum-like setting but you can also dine alfresco in the outside garden.
Explore: The Seaside
After lunch, we headed across the road from The Griswold to Sweet P’s, a super cute, pastel-colored ice cream store for a delicious sweet fix before meandering down the main street to the seaport. Here we marveled at the beauty and tranquility of the sea as we watched sailboats and boaters enjoying the water. ‘Droney’ was impressed, taking to the skies to capture this cute town and epic views of the ocean from above.
Stay: The Dean Hotel (Providence, RI)
A leisurely hour-ish drive took us to our digs for the night, The Dean Hotel, an elegant 52-room boutique hotel located in a historical 1912 building in Providence’s Downcity district. Here the vibe is old world meets new industrial with minimalist rooms filled with vintage furniture, art by RISD graduates, crafts by local artisans, and even a karaoke bar (no we didn’t try our luck). We did however enjoy a lovely dinner at North, the hotel’s on-site restaurant, popular with locals and visitors. Here the dishes come influenced by modern RI with seafood, and meat produced sourced from local farmers and fishermen and are best enjoyed shared. After we settled in for a nightcap and debrief at the hotel’s chic European-inspired The Dean Bar.
Day 2: Providence, Rhode Island ➝ Portland, Maine (via New Hampshire)
Drive time: 2hrs, 30 mins
We grabbed a coffee (chai tea in my case) and croissant and hit the road to discover the coastal charm of Portland. Rob at the wheel, our first stop was to take in the ocean air and grab a snap of beautiful Rye beach, then we were off to fulfill more of our lobster roll dreams.
Lunch: Ray’s Seafood (Rye, NH)
The best lobster rolls in the whole of New Hampshire can be round at Ray’s. We know this because we asked Bruce, who has been in the business of lobster rolls his entire life. It’s all down to the butter he says. At this delightfully authentic local gem (it oozed fisherman shack vibe right down to its red and white checked tablecloths, lobster nets out the back, and maritime images) we chowed down on clam chowder (delish) and warm New England rolls with, yep, just butter.
Lobster roll fix complete, we headed off in search of Lighthouses, which are a quintessential fixture on the New England coastline. Just 15 minutes north we came upon Portsmouth Harbor Lighthouse The only lighthouse on New Hampshire’s mainland, this lighthouse (also known as Fort Point Light) was built by the British in 1877 on the grounds of Fort Constitution, a Revolutionary War fortification. Today Portsmouth remains an important shipping port and the historic lighthouse, which offers open houses in summer, serves as a beacon of light for ships entering the harbor and New Hampshire’s 18-mile coastline.
Dinner: Eventide Oyster Co. (Portland, ME)
Back in the car, we headed north for an easy hour drive to Portland Maine, a super cute historic city on a peninsula extending into Casco Bay. The city is known for its Old Port waterfront where you’ll find working fishing wharves, chic converted warehouses, cute cobblestone streets with boutiques, and lively restaurants. We decided on dinner on the outdoor patio at Eventide Oyster Co., a trendy OG American oyster bar and James Beard Award-winning restaurant serving delicious fresh-caught oysters and shellfish, and their signature Brown Butter Lobster Roll. Spotting a theme yet?
Stay: The Press Hotel (Portland, ME)
Something of a journalist’s dream, The Press Hotel in the heart of Portland is located in the historic headquarters of the former Portland Press Herald, the state’s largest newspaper. The property is quirky and modern but goes out of its way to honor its legacy. Arty typewriter installations line the walls and everywhere you look are nods to typesetting and the media, the undoubted highlight being the elevators whose walls are adorned with the original print press. The lobby is the heartbeat of the hotel where you can lounge around over a coffee or cocktails and on the lower level is a permanent art gallery showcasing the works of local Maine artists.
Day 3: Portland, Maine ➝ Camden, Maine
Drive time: 1 hr, 30 mins
We started our morning strolling down the hill from The Press Hotel to the town’s village-style epicenter, marveling at the quaint cobblestoned streets, historic buildings, Victorian-era homes, and cute parks. Then it was back in the car for the 1.5-hour drive to the famed Red’s Eats (yep the lobster rolls were calling).
Lunch: Red’s Eats (Wiscasset, ME)
I hadn’t heard of Red’s Eats but Rob assured me, this was the place for some of the best lobster rolls in all of Maine, and judging from the endless line, it seems the rest of the country agrees. Located on Route 1, on the side of the road in Wiscasset, a leafy nineteenth-century village, next to the Sheepscot River, this humble red lobster shack has been a mainstay for over 80 years and a pilgrimage here feels almost religious. Founded by the late Al ‘Red’ Garnon, Red’s Eats has won multiple awards for its rolls, an overflowing mound of sweet, chunky meat in a buttery, grilled cradle. ‘Red’ started his rolls after being disappointed by some he’d tasted and this family business is now run by his grandkids. Warning the lines are ridiculous, but it’s worth the wait. That said, if patience isn’t your game, head across the road to a little sea-faring hub where you can pick up a great chowder and roll at Sprague’s Lobster.
Explore: More Maine Lighthouses
As we discovered Lighthouses and coastal bluffs are plentiful in New England so we did a bit of hopping. In under an hour from Red’s you can stop to enjoy the views and history of Marshall Point Lighthouse, Owls Head Lighthouse, Rockland Breakwater Lighthouse, Curtis Island Lighthouse providing of course the famous New England fog behaves (sadly for us it didn’t). Though we did get a decent glimpse of Marshall Point Lighthouse, perhaps the most well-known in these parts, which stands on a rocky point at the end of the St. George peninsula marking the entrance to the mouth of the St. George River and harbor of the fishing village of Port Clyde. It was well worth the hike.
Dinner: The Waterfront (Camden, ME)
A short drive from Marshall Point and we arrived at Camden Maine home for the night. Here the locals will all testify you must experience and dine at The Waterfront and their recommendation was bang on point. This stylish, harborside (right on the water) eatery and bar serves some of the best seafood in the area (all freshly caught by local fishermen). Pull up a seat on the outdoor patio and tuck into the lobster cobb salad. Who said we can’t mix it up?
Stay: Whitehall (Camden, ME)
Like all of New England, Camden Maine is fairytale pretty and Whitehall is as pretty as a picture. This delightful property, by boutique group Lark Hotels, was originally an 1834 Sea Captain’s house but today evokes more of a coastal mansion. Set on an expansive lawned area with rambling porches, rocking chairs, fairy lights, and fire pits, this luxe inn honors its history (famed poet Edna St. Vincent Millay was discovered here, after reciting one of her works during a summer party) while celebrating bold, bright, modern design. Everywhere you look there are pops of red (you can’t miss the statement shiny red leather banquette sofa), turquoise (on the stairs and wallpaper in the suites), and every color of the rainbow, juxtaposed against weathered woods, aged metals, sailors rope, and coastal decor.
Day 4: Camden, Maine ➝ Kennebunkport, Maine
Drive time: 2hrs, 10 mins
We woke up here and had a breakfast (simple but quaint and local products), then grabbed a coffee and some pastries for the road from that super cute artisanal coffee shop, before heading out in search of more lobster rolls and lighthouses, both of which are glorious at Cape Elizabeth.
Lunch: Bite into Maine (Cape Elizabeth, ME)
Another day, another lobster roll, and today’s lunch came straight out of the super cool food truck, Bite into Maine manned by three super cool dudes. These guys specialize in traditional and quirky takes on the famed New England lobster roll, with freshly baked bread, fresh Maine lobster, real butter and their signature mayos; Maine style (mayo and fresh chives), CT (warm butter only), Picnic Style (coleslaw, celery salt, and butter), Chipotle (smoky chipotle mayo) Wasabi (zingy wasabi mayo), Curry (yellow Indian curry). Out to rival the rolls is their hearty clam chowder and delicious lobster bisque. All of which is as outstanding as the surroundings.
Explore: Cape Elizabeth, ME
You’ll find Bite into Maine in stunning Cape Elizabeth, a leafy, coastal town near Portland. Home to history, shoreside parks, and yep lighthouses aplenty, the food truck is set inside Fort Williams Park right by Portland Head Light built in 1791 making it the oldest and most photographed lighthouse in the US. Today the light is automated and its keeper’s house is a museum, but just marvel at it from the shore or capture its magnificence from the sky if you’re “Droney”. This is the perfect picnic spot which is precisely what we did to devour our latest lobster roll feast. After, take a stroll around Fort Williams Park, once a bayside Army installation to explore the Arboretum trails and the fort’s old batteries.
Stay: White Barn Inn (Kennebunk, ME)
An hour south of Cape Elizabeth takes us to the quaint, lively town of Kennebunkport (cutest name ever). Historically a fishing and shipping village, this east coast summer playground, long beloved by the Kennedys and high-society, on the east coast for its New England charm, boutique hotels, and gorgeous beaches. Just accross the river at Kennebunk, we checked into the luxurious White Barn Inn & Spa, part of the Auberge Resorts Collection and never wanted to leave (so we didn’t). We perched up at the bar for a sunset cocktail served by master mixologist in dinner jacket and bow tie and just stared at the beamed ceiling and delighted in every inch of the rustic glamour of the 1860 era barn which is also home to The White Barn, the resort’s signature restaurant where we had an outstanding dining experience thanks to the Kennebunkport lobster with champagne lobster sauce. Oh my. Helmed by executive chef Matthew Padilla, the New England meets Maine-centric cuisine is truly special, just like the property. Here you can take your pick from the chic nautical inn-style suites or your own waterfront cottage. Divine.
Day 5: Kennebunkport, Maine ➝ New Haven, Connecticut
Drive time: 3 hours, 30 mins
After bidding a sad farewell to the stunning White Barn Inn, we headed into Kennebunkport to explore the cute town and immerse ourselves in its history. Don’t miss seeing the historic sea captain mansions that line Summer street, the summer cottages on Grace Ocean Ave, and the many local museums including Bush Family Museum, (an homage to the presidential family that spent their summers here), Brick Store Museum, and the Nott House.
Lunch: Max Downtown (Hartford, CT)
We arrived in Connecticut in time for lunch (yes this is something of a foodie road trip) where we settled in at the impossibly chic Max Downtown, a cool modern cool chophouse, that stands as a flagship restaurant in the state’s capital of Hartford. The vibe here is rich and old-worldly and judging from the food and drinks (it’s also a whiskey bar) it’s not difficult to see why it’s the winner of many a culinary award. Go for the Steak Frites and Pan-Seared Colossal Shrimp, they certainly put a smile on our faces.
Explore: Yale University Campus (New Haven, CT)
Who says you can’t go to Yale? OK, they didn’t let us in but just walking its perimeter and marveling at the architecture, historic stone buildings, awe-inspiring churches, and turrets of this legendary ivy-league university is an experience in itself. Afterward, head for a cocktail at Ordinary, a warm, cozy wooden walled tavern (New Haven’s oldest) two blocks from the campus to mix with the scholars and philosophers.
Dinner: Atelier Florian (New Haven, CT)
After such a delicious lunch, we didn’t think our culinary expectations could rise any further but Atelier Florian swiftly sent us back into a food coma in the best possible way. IF Max’s was warm and moody, this bistro-style favorite was bright and airy, a little Paris meets New England in its charm and design. As for the far, fresh sea-to-table dishes are the order of the day and there’s a focus on sustainable, local meat and produce and plenty of healthy vegan and gluten-free options. Rob doubled down and went for yet another lobster roll, while I went for my stalwart beer-battered fish and chips.
Stay: Graduate New Haven
Graduate Hotels, all positioned in flagship university towns, take highly conceptual design and a whimsical totally immersive experience to an entirely new level. No two hotels are alike and all pay homage to their respective university and their surroundings. Stepping into the Graduate New Haven was like stepping onto the set of a Wes Anderson movie – one filmed at Yale in its retro heyday. It’s hard to highlight all the standouts but you will be in awe of every well-thought-out detail from the “campus’ library, the black and white checkered floor, the retro wood paneling, the old-school telephone booth, and kitsch font.
Day 6: New Haven ➝ New York (via Connecticut)
Drive time: 2 hours
All good things must come to an end. We said goodbye to New Haven, any dreams we had of getting into Yale and our lobster, lighthouse and coastal charm immersion and hit the freeway back to the concrete jungle where more dreams are made off. Breakfast was coffee (chai tea for me remember) and pastries on the go, so naturally we went out of our way for one final pitstop.
Lunch: A Flyby at Delamar Greenwich Harbor (Greenwich, CT)
Located harborside with its own private dock in Fairfield CT, Delamar Greenwich Harbor is a luxury hotel that exudes New England charm with a European sensibility. If you choose to stay the property has one and two bedroom suites with spacious living rooms, some with terraces and beautiful views as well as a gorgeous onsite spa. Alas for us, life on the road meant we could just enjoy a drink and lunch. Not that we’re complaining given we got to dine at the iconic L’Escale, where the seasonally-inspired Mediterranean cuisine by award winning Executive Chef Frederic Kieffer almost transported us straight to the Côte d’Azur thanks to its two-hundred-year-old stone terracotta tiled floor, wood burning fireplace and wrought iron tonnelle covered waterfront terrace. Our pick? The salad nicoise, lobster sliders and Maine lobster fettuccine. I mean, why not?