Lost in New England: A Summer Road Trip Adventure

Five years ago, I embarked on one of my favourite road trips to date along the East Coast, exploring the charm and beauty of New England. From quaint covered bridges, mouthwatering seafood and picturesque coastal towns, I was instantly smitten. That trip still remains as one of my most popular blog posts to date. Returning to this region, I was excited to revisit some familiar spots as well as discover new gems. New England is a vibe and there’s just something about it that evokes a sense of nostalgia within me. Here's a summary of my New England road trip!

Day 1 & 2: Embracing Nature and Seaside Beauty

Hike at Mount Willard, NH
Rikki and I started the trip with an invigorating hike at Mount Willard. We had been before, but I will never tire of the summit views. If you're coming from Ontario or one of the eastern provinces, stopping in New Hampshire for this rewarding hike is a must. It’s about a 2 hour, 5km hike. The panoramic views from the summit are absolutely worth the effort, showcasing New England's natural splendour at its finest.

Stay at York Harbor Inn, Maine
York Harbor Inn is the perfect mix of relaxation and seaside charm. With six separate lodges catering to every budget and taste, it was the perfect starting point for our adventure. My room felt just like a cozy nook in a summer cottage, especially with the bay window giving it that extra touch of comfort. We stayed at the Harbor Cliffs, which offered stunning views of the ocean. The room was incredibly cozy, and the soothing on site jacuzzi was the perfect way to unwind after a day of exploring.

Drinks at Chapman Cottage at York Harbor Inn, Maine
After a long hike and drive, unwinding with pre-dinner drinks and appetizers at Chapman Cottage, part of the York Harbor Inn, was the perfect choice. The charming yellow building, perched atop a hill with stunning ocean views, set the scene for relaxation. We kicked back on the patio, savouring an ice-cold beer and crisp white wine. Their menu features craft beer, wine, and tasty bites.

Dinner at 1637, York Harbor Inn
Indulging in a delicious lobster feast at the inn's renowned restaurant, 1637, was an absolute treat. The ambiance was warm and inviting, with soft lighting and an elegant yet cozy atmosphere that made me feel instantly at ease. Large windows framed beautiful views of Harbor Beach, adding a picturesque backdrop to the dining experience. I had been craving lobster since the planning of the road trip, and this was my first opportunity to satisfy that craving. The lobster flatbread was tasty, each bite bursting with fresh, succulent lobster meat, perfectly complemented by the crispy crust. It was a great dining experience that truly captured the essence of coastal cuisine and set the tone for many great meals ahead.

Visit Hartley Mason Reserve & Harbor Beach at Sun
After dinner, we made our way to Hartley Mason Reserve and Harbor Beach, which are conveniently located right across the street from York Harbor Inn. This spot quickly became one of my favourite places to unwind. As the sun began to set, we strolled along the beach barefooted and watched as the sky transformed into a canvas of vibrant colours. The hues of pink, orange, and purple reflected off the wet sandy beach, creating a mesmerizing and almost surreal scene. The gentle sound of the waves and distant caws of seagulls added to the tranquil atmosphere, making it a perfect end to the day. Watching the sunset here was truly an unforgettable experience, a moment of pure beauty that felt almost too perfect to be real.

Day 3 & 4: Coastal Charm and…a Taylor Swift Impersonator?

Things to Do:

Visit Portland Head Light, ME
I love lighthouses, so visiting Portland Head Light in Maine was a must for me. Known as the most photographed lighthouse in the state, this iconic beacon did not disappoint. Nestled on the rugged shores of Fort Williams Park, the lighthouse stands against the beautiful coastal scenery, making it an ideal spot for capturing postcard worthy photos. Fun fact: Portland Head Light is the oldest lighthouse in Maine, commissioned by George Washington in 1791!

Walk Around Portland, ME
Strolling through the charming cobblestone streets of Portland was the perfect way to spend an afternoon. The local culture and vibrant coastal atmosphere was a vibe. One of the highlights was visiting a bustling fish market, where the authenticity of the experience truly shone through. The market was brimming with a dizzying array of fresh seafood, and the variety of oysters alone was staggering. Watching the locals stock up on their favourites made me almost envious of their regular access to such bounty. The sights, sounds, and smells of the market offered a genuine slice of Portland life that I highly recommend to anyone visiting this delightful coastal gem.

Canobie Lake Park, Taylor Swift Tribute
About a week before our trip, Rikki sent me a TikTok of what I initially thought was Taylor Swift. However, after looking closer and reading the comments, I realized it was a Taylor Swift impersonator. Most comments were very positive, with some locals noting that Canobie Lake Park is well-known for having excellent impersonators. As a Swiftie, I figured this was the closest I’d get to a Taylor Swift show, given the high ticket prices and my luck with the lottery system for her Toronto concerts. Canobie Lake Park also offers fun rides, which we enjoyed, but the highlight was the Taylor Swift Tribute Show. The park, famous for its great tribute shows and impersonators, did not disappoint. The show was fantastic, featuring some of Taylor’s biggest hits, and is a must-see.

Eat:

Lunch at Bite Into Maine, Allagash Brewing Location
Savouring a flight of lobster rolls paired with craft beer at this popular lunch spot was a treat after exploring Portland. Bite Into Maine offers a variety of rolls and even a Lobster Flight where you can try three types: the classic Maine roll with fresh lobster and mayo, the warm and buttery Connecticut roll, and the unique Picnic roll with celery salt, chives, and coleslaw. It's a must-visit for lobster roll lovers. They’re not heavy on the mayo so the lobster really shines through!

Stay:

935 Ocean Beachside Inn, Hampton, NH
Staying at 935 Ocean Beachside Inn provided cozy comfort and stunning ocean views. Though our night here was brief, not allowing us to fully enjoy the nearby beach, it served as the perfect base for our New England adventures, offering major surf town vibes.

Day 4 & 5: Rustic Elegance and Coastal Exploration

Stay:

Briar Barn Inn, Rowley, MA
After a long day, there’s no better feeling than checking into a comfortable inn for the evening. Briar Barn Inn is a charming countryside retreat that perfectly combines rustic elegance with modern comfort. The inn features spacious, beautifully designed guest rooms that provide a perfect blend of charm and luxury. Our room was particularly memorable, featuring a cozy fireplace that added to the ambiance and provided a nice touch of comfort during our stay. Although we were in the middle of summer, I can only imagine how cozy it would be in the fall and winter months.

The inn's amenities include an on-site spa, where guests can indulge in a variety of rejuvenating treatments, and a serene pool area, perfect for a relaxing swim, or in my case, a morning dip. The tranquil setting and impeccable service made Briar Barn Inn an ideal place to unwind and escape after our adventures during the day. Treating myself to a rejuvenating facial at the Briar Barn Inn spa was a highlight of the trip. It was the perfect way to relax after days of exploring New England.

Things to Do:

Explore Newburyport and Gloucester, MA
Exploring Newburyport and Gloucester revealed coastal charm, unique shops, and delicious restaurants. Both of these towns are quintessential New England and we really enjoyed exploring the streets. In Newburyport, I loved Partridge in a Bear Tree (pictured below), which made the Christmas lover in me feel right at home.

Eat:

Brunch at Grove, Briar Barn Inn, MA
Enjoying brunch at Grove, the inn's farm-to-table restaurant, was a great experience. The restaurant's interior is designed to resemble a beautiful modern barn, with high ceilings, exposed wooden beams, and windows that allow natural light to flood the space. Fresh florals and rustic chandeliers add to the charming ambiance, creating a warm and inviting atmosphere.

My breakfast sandwich, served on a toasty fresh croissant, was absolutely delicious. The croissant was perfectly flaky and buttery, and the filling was a harmonious blend of savoury ingredients that left me craving more. The attention to detail in both the presentation and the flavours made the meal truly memorable. Dining at Grove was a highlight of my stay at Briar Barn Inn, showcasing the best of local ingredients and culinary expertise in a stunning setting.

Seaport Grille in Gloucester, MA
Dinner at Seaport Grille featured a fantastic meal with clam chowder, fish and chips, and a blackened shrimp Cobb salad. The perfectly cooked fish and chips and seasoned-to-perfection blackened shrimp made for an unforgettable dining experience by the sea.