Ness' bit of everything

14 Day New England Road Trip Itinerary

Introduction
Parts of New England had been on my travel list for quite some time. I was drawn by the charming houses, rugged coastlines, and the promise of incredible food. I was keen to experience both the buzz of the larger towns and the irresistible charm of the smaller ones.

We chose to fly in and out of Boston, heading south first to explore parts of Massachusetts and the beautiful Cape Cod coastline. From there, we headed north through Connecticut and into Maine, where we spent most of our time, soaking up the peaceful small-town atmosphere and immersing ourselves in nature.

Planning the Trip
I find a lot of my travel inspiration on Instagram, following the journeys of other travellers. From there, I start creating lists of places to visit, restaurants to try, hotels to stay in, and things to do – usually organised in Notion. Recently, I’ve also started using Milanote to plan my trips. It’s a brilliant visual tool that allows you to map out your itinerary with photos, links, and notes in an easy-to-follow flow.

I also save most places as favourites on a Google Maps layer, so I have everything handy once I’m abroad.

We love a good road trip, but we’ve learned from experience that moving on every single night can be exhausting. It’s difficult to settle, and you end up seeing less of each place. Now, we like to book somewhere for a larger chunk of time, ideally somewhere central to the areas we want to explore, and use it as a base for day trips. This way, we get the best of both worlds — the freedom to discover new places without the constant packing and unpacking.

Day-by-Day Breakdown

Day 1 – 2: Boston, Massachusetts
We landed around 5pm, which turned out to be the perfect time for managing jet lag – just a couple of hours to stay awake before bed. We stayed in the South Boston Waterfront area, mainly because we needed access to parking. After grabbing dinner near the hotel and sorting our suitcases, we headed straight to bed.

One of the few perks of flying west from the UK is the early mornings thanks to jet lag. If you manage to get back to sleep at 3am, you’re doing well – and by 6:30am, you feel so sprightly! We headed into town early, stopping off at the gorgeous Tatte Bakery & Café for coffee and pastries.

Our first activity was exploring the Freedom Trail – and I couldn’t recommend it enough. It’s a fantastic way to see different parts of the city while learning about Boston’s interesting history. Just make sure you’re wearing comfy shoes for all the steps – there’s quite a bit of walking!

Afterward, we took a trip out to Harvard to wander around the iconic campus. For dinner, we headed to bartaco, which hit the spot perfectly. And, of course, after a full day of exploring, we ended the night with… an early bedtime!

Recommendations for Boston

To do

• See a Red Sox game
• Wander around Harvard
• Walk the Freedom Trail 

Food

• Tatte Bakery & Café for coffee and pastries
• Mike’s Pastry for the famous cannoli 

Day 3 – 7: Cape Cod, Massachusetts
An early night meant an early morning, so we hit the road bright and early, heading south to Cape Cod.

Our first stop was in the charming town of Scituate, where we visited the Scituate Lighthouse and enjoyed a lovely lunch at Knead Bakery & Bistro. Continuing south, we made another stop in Plymouth to stretch our legs and explore the Pilgrim Memorial State Park.

Driving south and then crossing the bridge onto Cape Cod felt like the real beginning of the coastal part of our trip. We checked into the Bluebird in Dennis Port, then headed straight out for seafood at Brax Landing, where we were treated to a stunning sunset over the harbour by the open firepit.

The next morning, we fuelled up with breakfast at Good Friends Café  – I went for the pancakes, of course! From there, we spent the day exploring different towns along the Cape, taking our time and soaking in the charm. One highlight was walking the loop trail at Morris Island, a peaceful and scenic spot with gorgeous views.

We grabbed lunch at The Knack, where the burgers were absolutely delicious, before making our way to Provincetown. This was a real highlight and not what I expected it to be at all – it was vibrant, quirky, and bursting with life and art.

Later in the evening, I wandered down to the beach near our motel for a dip in the sea and to chill. It was the perfect way to wind down after such a packed day. 

On our third day on the Cape, we decided to take things a little slower and skip the long drives. After coffee and pastries from Lighthouse Keeper’s Pantry, we headed to Bass River Kayaks to rent some kayaks. I couldn’t recommend them highly enough – their equipment was well looked after, and the safety briefing was very thorough and reassuring.

We spent the morning exploring the Bass River, taking in the peaceful scenery from the water, admiring the beautiful coastal homes, and spotting local wildlife along the way. It was such a refreshing change of pace and a brilliant way to see the area from a different perspective.

Afterwards, we treated ourselves to ice cream from Holy Cow in Dennis – the perfect reward after a morning of paddling, yum! 

Recommendations for Cape Cod

To do

• Take a trip to Martha’s Vineyard or Nantucket
• Explore Provenance town 
• Explore the beaches 

Food

• Holy Cow Ice Cream Café in Dennis
• Lighthouse Keeper’s Pantry in Yarmouth port for coffee, breakfast pastries, lunch sandwiches, sundries
• Captain Parker’s in Yarmouth for classic fried seafood and clam chowder
• The Knack, fast-casual but really delicious
• Brax Landing in Harwich port or Fisherman’s View in Sandwich for a waterfront dinner
• Good Friends Café in Dennis or Café Chew in Sandwich for breakfast

Day 7 – 12: Kennebunkport, Maine
We checked into the very quaint Mabel’s House and spent the afternoon settling in and exploring the nearby beach.

The following day, we borrowed bikes from the guest house and cycled along the coastal road. We’re a bit obsessed with New England houses, so we loved admiring the seaside homes along the way – and even spotted the Bush family compound on our route. We stopped for coffee at Dock Square Coffee House, then later decided to make the most of the guest house’s kayaks too.

Paddling up the Kennebunk River with the tide was one of my favourite parts of the whole trip. Timing it with the tide really helped – the current’s strong, so we wanted it working in our favour! We kayaked miles upstream, passing through town and into more rural stretches, before letting the outgoing tide carry us back downstream.

After such an active and fun day, we rewarded ourselves with lobster rolls from The Clam Shack – and yes, they absolutely lived up to the hype. We finished the day at Cape Porpoise, watching the sunset. 

The next day, we set off for Portsmouth, New Hampshire, but couldn’t resist a stop at Kittery Point after hearing rave reviews about Lil’s Café. We arrived on a Sunday morning and the place was absolutely buzzing – packed with locals grabbing their weekend coffee and pastry fix. It did not disappoint. We got chatting to a few friendly regulars who insisted we try the blueberry muffin – a very good call. The whole place had a brilliant community vibe.

What I hadn’t realised was that a U.S. Naval Shipyard is located nearby. Curious, I wandered a bit too close to the entrance gate for a nosey –  and promptly got shouted at by US military guards, machine guns and all! Definitely one of the more unexpected parts of the trip…!

After all that excitement, we thought it best to make a swift exit and continued on to Portsmouth, our planned stop for the day. We spent a relaxed afternoon wandering around the charming seaport town and grabbed some lunch before heading back. That evening, we headed to Nubble Lighthouse at Cape Neddick in York – an absolutely stunning spot. The golden hour light made it even more magical. We topped off the day with the biggest ice cream ever, enjoyed with a view. A sweet ending to a great day.

On our final full day in Maine, we made our way to Portland for a pre-booked sailing trip with Portland Schooner Co. The two-hour cruise took us around Casco Bay aboard a beautifully restored traditional schooner.

It was such a memorable experience – there’s something incredibly calming about being out on the water, sails billowing, with views of the coastline drifting by. The crew were fantastic, sharing stories and insights about the area’s maritime history as we sailed past lighthouses, islands and lobster boats. Seeing the bay from the water gave us a whole new perspective on the area.

After we docked back in the harbour, we were in need of a coffee fix. We headed to Double Great Coffee, a neighbourhood spot in Munjoy Hill that was full of locals. While chatting with a few friendly regulars, they tipped us off about a great lunch option nearby – the Eastern Prom Food Truck Park. We followed their advice and were rewarded with delicious Vietnamese sandwiches, enjoyed with a view over the water.

Recommendations for Maine

To do

• Visit Acadia National Park
• Visit Kennebunkport
• Boat trip in one of the bays/harbours
• Ogunquit Beach
• Cape Neddick Lighthouse “Nubble Lighthouse”

Food

• The Clam Shack, Kennebunk Port for lobster rolls 
• Lils cafe, Kittery for amazing baked goods and coffee with a neighbourhood vibe
• Anju Noodle Bar, Kittery for fresh and taste ramen

Day 12 – 14: Acadia National Park, Maine
We packed up and got in the car for the 3 hour drive up to Bar Harbour on mount desert island. We checked into our motel and had an exploration around the town, around the waterfront. It is a gorgeous picturesque town with views over the islands and boats in every direction. We wandered into the shops.

The next day was all about Acadia National Park. We secured our permit and headed in early, knowing the park gets much busier and hotter by lunch time. A lot of the scenic loop operates as a one-way system, so it’s worth planning ahead. We had a few hikes in mind and wanted to make the most of the cooler, quieter part of the day.

The Beehive Trail – and what an experience! It’s unlike any other hike I’ve done: steep, rocky, and fitted with iron rungs to help you scramble up the face of the mountain. I wouldn’t have fancied it in the rain, but in dry weather, it was amazing. The views from the top were absolutely worth it. Afterwards, we drove the Park Loop Road, taking in the stunning coastal scenery and eventually winding our way up Cadillac Mountain for even more panoramic views.

The following day, we explored the quieter western side of the park. Again, we headed out early and took on the Acadia Mountain Trail – another brilliant route with rewarding views. After the hot, dusty hike, Echo Lake looked too tempting to resist. I’d heard it was one of the best freshwater lakes in the park for swimming, and it didn’t disappoint. We found a peaceful access point at Ike’s Point and took a well-earned dip – the perfect way to cool off. Later in the afternoon, we drove to Bass Harbor Head Light Station, then over to the Seawall picnic area, where we ate lunch right by the shoreline. 

Back in Bar Harbor, it was time to face the sad task of packing. But we wanted to end on a high note – with Rosalie’s Pizza, a local favourite. We picked up a takeaway and walked to Agamont Park, where we ate overlooking the harbour and bay as the sun set. It was a simple but perfect way to mark the last evening of both Acadia and the entire trip.

Our final day was all about travel – retracing the long drive we’d taken throughout our journey, heading back to Boston for our evening flight home.

Recommendations for Acadia National Park

To do

• Hike the Beehive Trail
• Drive on the Park Loop Road
• Visit Jordans Pond House 
• Swim in Echo Lake 

Food

• Mount Dessert Bakery, Bar Harbour for great breakfast bagels and coffee
• Rosale Pizza in Bar Harbour for you guessed it, pizza.

Final reflections

This road trip through New England was everything we hoped it would be – a perfect blend of adventure, charm, and relaxation. We struck a balance between exploring new places and staying grounded long enough to truly soak in the surroundings. I particularly loved the active parts of the trip – from cycling along coastal roads to paddling up rivers and going on scenic hikes. Acadia National Park, in particular, offered some of the most memorable.

One thing we did learn was that eating out in the U.S., while often delicious, can feel quite heavy over an extended trip. Especially when breakfast wasn’t included and we found ourselves eating three meals out each day. We started to make better use of supermarkets – picking up things for breakfast or picnic lunches – and it made a big difference, both in how we felt and in balancing the budget.

Next time, I think we’d book more accommodation with kitchen facilities or opt for the occasional Airbnb, just to give ourselves the option of a home-cooked meal in the evenings.

New England truly charmed us. From its coastal beauty and historic towns to its food, friendly locals, and natural spaces – it’s a region I’d recommend wholeheartedly to anyone planning a trip to the East Coast of the U.S.

Are you planning a US road trip? If so, what are your plans?

Ness x