The Perfect 4-Day New England Road Trip Itinerary

There is something about New England that feels like it was specifically designed for a road trip. Coastal towns. Tiny coffee shops. Historic streets. Mountains appearing out of nowhere. Lobster rolls. OMG, SO MUCH LOBSTER. Roadside stops you absolutely did not plan for. And an alarming number of places that make you say, "Wait, this is SO cute."

Truthfully, this trip started on a whim—and it ended up being one of my favorite road trips we've ever taken.

WATCH HERE: https://www.youtube.com/watch?v=haJU_DbhINM&list=PLYB5FTvCo3wI 

We flew into Boston, spent some time with friends, rented a car, and then made our way up the coast toward Portland, stopping whenever something caught our eye. There was no attempt to see all of New England in four days (because, impossible), and I think that's part of why I loved this trip so much.

We wandered through bookstores, ate an unreasonable amount of lobster, antique shopped our way through tiny towns, drank coffee on the side of a cliff, and found a few places I already know I'll go back to.

There is SO much more to see (Bar Harbor, I'll be back 🤍), but if you're planning a New England getaway of your own, these were our favorite stops along the way.

Day 1: Boston

Our New England adventure started in Boston, and we packed a surprising amount into our first day without making it feel like we were racing around the city. We started with some of the classics: Boston Common and the Freedom Trail, before making our way into Beacon Hill. And Beacon Hill? Exactly as charming as advertised.

Walk Acorn Street, wander through the neighborhood, and, one of my personal recommendations, give yourself time to browse the little bookstores tucked throughout Beacon Hill. This is not the portion of the trip to be in a hurry.

We also explored around the Paul Revere House before making one of the most important stops of any Hello From Cass itinerary: coffee.

Coffee Stop: Tatte Bakery & Café

Tatte is a great place to grab coffee and something to eat before continuing around the city. Cute? Yes. Delicious? Also yes. We're off to a strong start.

If you're traveling with kids, I'd also recommend the Boston Tea Party Ships & Museum. It's interactive enough to keep younger travelers interested while still giving everyone some genuinely fascinating Boston history.

Before wrapping up the day, we drove by Fenway Park and headed toward the waterfront for seafood.

Don't Skip: Lobster at Legal Sea Foods

When in New England... Our first lobster of the trip happened at Legal Sea Foods, and a waterfront seafood dinner felt like the appropriate way to officially kick off the road trip. Little did we know how much lobster was still in our immediate future.

Day 2: Boston → Essex → Ipswich → Portsmouth → Kittery

Day two is when the real road trip began. We picked up the rental car, left Boston behind, and started making our way north with one major rule:

If something looked interesting, we could stop. That mentality ended up creating some of my favorite moments of the entire trip.

First Stop: Woodman's of Essex

Come hungry. And if there's a line, don't let it scare you. Woodman's of Essex was our lunch stop and absolutely worth adding to the route. Afterward, we spent some time browsing the antique shops around Essex, which, if you know me, was obviously going to happen. 

New England and antique stores are a dangerous combination for both my schedule and my luggage. Bonus bean and I both walked away with cool vintage treasures to take home!

Ipswich + Castle Hill on the Crane Estate

From Essex, we continued to Ipswich, another ridiculously charming Massachusetts town worth slowing down for. One of the highlights here was Castle Hill on the Crane Estate.

If historic estates, sprawling grounds, coastal views, or simply pretending you live somewhere significantly more extravagant than you actually do sounds like your thing, add it to the list. It's gorgeous.

Portsmouth, New Hampshire

Then came one of the biggest surprises of the trip: Portsmouth. We initially planned it as another stop along the route, and it ended up being one of my favorite towns of the entire trip. 🤍

It's walkable, historic, charming without feeling overly touristy, and exactly the kind of place where I could have happily spent much longer wandering around. We eventually continued into Maine and spent the night in Kittery, perfectly positioned for the next day's coastal adventure.

Day 3: Kittery → Ogunquit → Kennebunkport → Arundel → Portland

If I had to pick one day that encapsulates everything I wanted from a New England road trip, it might be this one. Ocean views. Tiny towns. Coffee. Lobster rolls. Antiques. A very strong itinerary.

Morning in Ogunquit

We started the day in Ogunquit with a walk along Marginal Way, a gorgeous coastal path that takes you along the cliffs and into Perkins Cove.

Give yourself time here. This isn't a "take one picture and leave" kind of stop.

Walk around Perkins Cove, browse a little, enjoy the views and then, obviously, find coffee. We stopped at Wild Valentine before continuing up the coast.

Coffee With a View

Yes, we'd already had coffee. No, that did not stop us from getting another one, haha!

Our second coffee stop was Bald Head Coffee at Cliff House, and this one came with a cliffside view. There are coffee runs, and then there are coffee runs in Maine overlooking the Atlantic. Different category entirely. Bonus bean could have spent HOURS running around the cliffside, and honestly we could have too. Photos just don't do the experience justice and it's a dream to stay at this resort venue!

The Best Lobster Roll of the Trip

Next up: Brix + Brine. And I'm making the executive decision to put this in writing:

Best lobster roll of the trip. There were multiple contenders over these four days, so I do not make this declaration lightly. If you're following this route, put it on the list.

Kennebunkport

From there, we explored Dock Square and the harbor in Kennebunkport, which is every bit as quintessentially New England as you'd hope. We also made our way to Goose Rocks Beach, another stop worth building into your drive if you have the time.

One of the best things about this entire trip was that none of these stops required an enormous commitment. We'd explore, walk around, grab something to eat or drink, and then get back in the car whenever we were ready. No rushing. No checking attractions off a list just to say we'd been there.

Antique Shopping in Arundel

Naturally, we needed another antique stop. If you're an antique lover too, Antiques USA in Arundel is worth adding to your route. My road trip philosophy is that there is always room in the car for one more vintage find. Whether the people traveling with me agree with this philosophy is irrelevant.

Portland Head Light

Before heading into Portland, we stopped at Portland Head Light. And THIS is one of those places that immediately makes you think:

Oh. I'm in Maine. Rocky coastline. Lighthouse. Ocean. All of it. It's iconic for a reason.

We finished the day with dinner in Portland followed by a sunset stroll through the Old Port cobblestone streets, historic buildings, little shops, restaurants, and the waterfront. After a full day of road-tripping, it was the perfect place to slow down for the night.

Day 4: Portland

Our final morning was dedicated to Portland before heading back to the airport. We started with a morning walk through the Old Port, which I highly recommend seeing both at night and in the morning. Same neighborhood, completely different energy.

There were also a few very important missions to accomplish before leaving Maine.

A Few Portland Favorites

We picked up caps from Bomdia, browsed Blanche + Mimi, and perhaps most importantly, got a potato donut from The Holy Donut.

Yes, a potato donut.

Yes, there may be a line.

Yes, it's worth it. 🍩

And because apparently one visit wasn't enough, we made one last stop at Portland Head Light before finally heading to the airport. No regrets.

What I'd Do Differently Next Time

Honestly? Give ourselves more time.

Four days worked beautifully for this route because we weren't trying to conquer New England. We picked a direction, had a handful of places we wanted to see, and gave ourselves permission to stop along the way. But this trip absolutely left me wanting more.

I'd spend more time in Portsmouth. I'd explore farther up the Maine coast. I'd dedicate more time to the tiny towns we passed through. And Bar Harbor? I'm coming for you. 

The Route

If you want to recreate our trip, here's the quick version:

Day 1: Boston
Boston Common → Freedom Trail → Beacon Hill → Paul Revere House area → Boston Tea Party Ships & Museum → Fenway Park → Waterfront

Day 2: Massachusetts → New Hampshire → Maine
Boston → Essex → Ipswich → Portsmouth → Kittery

Day 3: Coastal Maine
Kittery → Ogunquit → Kennebunkport → Arundel → Portland

Day 4: Portland
Old Port → shopping + donuts → Portland Head Light → airport

The Cass Road Trip Philosophy

If there's one thing I'd take away from this trip, it's this: Don't plan every second of a road trip. Know the places you absolutely don't want to miss. Save some restaurants. Have a general route.

Then leave some room.

Get the second coffee.

Take the scenic road.

Pull over because something looks beautiful.

Spend longer in the town you unexpectedly fall in love with.

Four days, three states, many cups of coffee, an impressive amount of lobster, and approximately 700 reasons to go back.

We already can't wait. 🤍

Cheers,

Cass