A Guide to New England: Portsmouth, York, Ogunquit + Boston š
Updated: 5 days ago
There are some trips you plan down to every last detail, and then there are trips where you visit a friend and somehow end up road-tripping through some of the prettiest places in New England. This was definitely the latter.
I visited during the fall, which meant colorful trees, crisp weather, coastal towns and basically every drive looking like it belonged on a postcard. We explored Portsmouth, New Hampshire, made our way up the Maine coast through York and Ogunquit, and spent time in Boston along the way.
This isn't meant to be an everything-you-need-to-know New England itinerary, but rather a look at the places we visited and some of my favorite stops along the way. If you're planning a fall trip to New England, hopefully this gives you a few places worth adding to your list!
š Portsmouth, New Hampshire
Stroll Dwontown Portsmouth
Save some time to wander and shop around downtown Portsmouth! The historic downtown is incredibly charming, with brick-lined streets, colorful storefronts and tons of locally owned boutiques, gift shops and specialty stores to pop into. You're also just steps from the waterfront, making it an easy area to explore without much of a plan.
Elephantine Bakery
Tucked down a cobblestone alley in downtown Portsmouth, Elephantine Bakery opened in 2018 as a European-inspired cafƩ after co-owner Sherif Farag trained in Paris. Even its name has a connection to Egypt, referencing Elephantine Island and an ancient bakery discovered there.
The cafƩ is tiny and popular, so expect a crowd and consider taking your order to go if you can't snag one of the few indoor or patio tables. I ordered the ham and cheese baguette, which was phenomenal, but they're especially known for their handcrafted pastries, breads and coffee.
We only scratched the surface of Portsmouth, but that's honestly a good reason to go back! This small coastal city was settled in 1623 and has centuries of maritime history tied to the Piscataqua River. Beyond wandering the boutiques and restaurants around downtown, you can explore the historic homes and gardens at Strawbery Banke Museum, walk along the waterfront at Prescott Park, explore historic Market Square or follow the Portsmouth Harbour Trail.
For us, the charm was really in simply walking around ā brick streets, historic buildings, little shops and the waterfront all within a relatively compact downtown. If you're road-tripping through New England, Portsmouth is definitely worth giving more than just a quick stop!
š York, Maine
We kept our time in York pretty simple and headed straight for the coast to see Nubble Lighthouse, and honestly, that alone was worth the stop! Officially known as Cape Neddick Light Station, the lighthouse was first lit in 1879 and sits on a tiny rocky island just offshore. It's still an active lighthouse today and has become one of the most iconic sights along Maine's coast.
You can't actually walk out to the lighthouse, but Sohier Park gives you gorgeous views from the mainland. We spent our time taking in the scenery and walking along the rocky coastline ā it felt like such a quintessential Maine moment. Fun fact: a photo of Nubble Lighthouse was even included aboard Voyager II as one of the images meant to represent Earth!
If you're road-tripping along the Maine coast, this is an easy, super charming stop to add to your route.
š¦ Ogunquit, Maine
We weren't in Ogunquit for long, but this little coastal town quickly became one of my favorite stops! We walked part of the Marginal Way, a 1.25-mile paved path along the rocky coastline with gorgeous Atlantic views, before wandering through the super-walkable downtown. We visited around Halloween, and the town went ALL OUT with the decorations, which made it even more charming. We ended our visit with drinks and live music around the piano at The Front Porch, an iconic Ogunquit piano bar that's been around since 1980.
Fun fact: Ogunquit grew from a fishing community into an artists' colony and seaside destination, and its name is traditionally said to mean ābeautiful place by the seaā ā which feels pretty fitting after seeing that coastline!
šļø Boston, Massachusetts
Take a Stroll in the Boston Public Garden
Take a break from exploring the city with a stroll through the Boston Public Garden! Established in 1837, it was Americaās first public botanical garden and is such a beautiful, peaceful spot right in the middle of Boston.
Pack a picnic, wander the paths or simply relax for a bit. We also stopped at the iconic Cheers bar right next to the gardens, making it easy to pair the two while exploring the area.
Definitely a must-visit in Boston!
Get a Cannoli at Mike's Pastry
You can't visit Boston's North End without stopping for a cannoli at Mike's Pastry! This Boston institution was founded by Italian immigrant Michael Mercogliano in 1946 and has been serving its famous cannoli on Hanover Street ever since.
And these aren't small cannoli! š They have a huge selection of flavors, all generously stuffed with filling. The shop is incredibly popular, and we actually had to wait outside just to get in, but thankfully the line moved quickly. Our massive cannoli were 100% worth the wait.
If you're looking for something sweet with a little Boston history mixed in, add Mike's to your North End itinerary!
Ciao Roma
If you're looking for that classic North End pasta experience, Ciao Roma is such a fun stop! Located right on the historic Freedom Trail overlooking North Square, the restaurant specializes in Roman-inspired Italian dishes and house-made pasta.
There are a few cozy seats inside, but on a sunny day, the patio is where you want to be. It has that perfect mix of energetic and buzzing while somehow still feeling intimate and romantic ā even though I was there for a girls' day. We loved sitting outside, eating pasta and taking in the atmosphere of one of Boston's most historic neighborhoods.
Fun fact: the restaurant actually started as Ciao Bella before reopening as Ciao Roma under the same ownership.
Alibi
Dinner, espresso martinis and dancing inside a former jail? This was such a fun Boston night out! Alibi is tucked inside The Liberty Hotel, which originally opened as the Charles Street Jail in 1851. Even cooler, the bar itself occupies the jail's former ādrunk tank,ā and you can still see original bluestone floors, brick cell walls and ironwork throughout the space.
We started the night with some phenomenal dishes and an espresso martini tree, then stayed as the night transitioned into more of a nightlife atmosphere and danced! If you're looking for a Boston spot that combines food, cocktails, history and a fun night out, Alibi is definitely worth adding to your list.
Rochambeau
Jazz + brunch might just be the perfect combination. Rochambeau is a Parisian-inspired French brasserie in Bostonās Back Bay, serving French classics with a modern twist. If you can, visit on a Sunday when they host live Jazz Brunch from 10 AMā3 PM!
We started with the raw oysters and French onion soup, both absolutely worth ordering, before I had the steak & eggsfor my entrƩe. And definitely save room for one of their unique desserts! Between the food, atmosphere and live jazz, this was one of those brunches that felt like an experience rather than just another meal.
Where to Stay:
Hotel AKA Back Bay
If you want to stay right in the heart of Boston, we absolutely loved Hotel AKA Back Bay! The location was one of our favorite parts ā you can easily walk to Newbury Street, Copley Square, the Boston Public Garden, restaurants, shopping and plenty of other Boston landmarks.
The hotel itself has a pretty cool history too: the building was constructed in 1926 as the former Boston Police Department Headquarters before eventually being transformed into a hotel.
Definitely don't skip breakfast at their onsite restaurant, The Berkeley. I had the steak and eggs and it was one of my favorite hotel breakfasts! The restaurant focuses on seasonal, New England-inspired dishes and also has two outdoor terraces.
Between the beautiful hotel, history and incredibly walkable location, I would absolutely recommend AKA Back Bay for a Boston trip!
Would I Recommend a New England Fall Trip?
If fall foliage, coastal towns and scenic drives are your thing, New England absolutely deserves a spot on your fall travel list. š
What I loved most about this trip was how easy it was to experience completely different places within a relatively small area. One minute we were wandering around Portsmouth, the next we were driving along the Maine coast, and then we were exploring the streets of Boston.
And honestly, some of my favorite moments weren't necessarily major attractions ā they were the colorful roads, little coastal stops and places we stumbled across along the way.
There's still SO much of New England I want to explore, so I definitely don't consider this my one-and-done trip. But for a first taste of the area during fall?
Portsmouth ā coastal Maine ā Boston was a pretty great place to start. š
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