New York to Maine the Perfect Dog Friendly 5 Day Road Trip Itinerary

I’ve been wanting to take a road trip from New York to Maine ever since I moved to the east coast. It’s popular as a perfect summer destination to escape the brutal heat of the city. This summer I finally did a five day road trip from New York to Maine with my boyfriend and our dog. I was truly blown away by the mild weather and beautiful surroundings.

Why Maine?

Being home to stunning coasts, charming light houses and some of the best seafood in the world, Maine really does deliver. When my boyfriend and I started planning our road trip we decided we really wanted to take our dog Chewy with us. We had no idea how pet friendly everywhere we went was going to be.

My road trip did have to focus on dog friendly activities and accommodations. But I would still recommend everything I did for anyone not traveling with their dog. Read on for the best towns to stop at and some of my favorite light houses.

Having the perfect road trip always requires a bit of flexibility. Take what I learned during my road trip from New York to Maine and plan your own perfect summer getaway.

More on Maine:

Click here for my list of favorite restaurants to stop at right near the coast. The post is full of fresh lobster spots, roadside eats and hidden coffee gems! Every place on the list is also pet friendly!

Planning for your road trip

Looking for the perfect route for a road trip is always the first step. I am the biggest fan of taking the long way. I flew past New York and through 11 countries before finally making my move to the big apple stick. It was there that I learned that the long way is the best way. Taking time to appreciate a small coastal highway and finding a road side lobster stand or cute coffee shop to refuel at is what road trips are all about.

My first instinct when traveling is to go go go. Get up early, be the first person there, and try like hell to squeeze everything in. This is something I had to fight drastically while in Maine. There is nothing that will kill a road trip faster that rushing through it. So I recommend taking it easy on the first day without too much pressure of a timeline.

Day 1: Going Through Providence and Boston to get from New York to Maine

On day one, we set Providence, RI as our first destination from New York City. This long road trip seemed like the perfect opportunity to stop through some Northeastern towns that I had never had an opportunity to see. Providence seemed like a good place to stretch our legs and get something to eat.

We left New York City around 11 am and were in Providence a few hours later, just in time for lunch. From there we went a little out of our way to drive through Boston. Boston is one of my favorite cities in the country and I will use any excuse to see it. My boyfriend Ryan has never actually been and it was a great tease for a trip we are planning later this year.

Stop in Salem

An unexpectedly awesome pit stop on our way from New York to Maine was Salem, Massachusetts. I have to admit that when I was younger I was completely obsessed with the idea of being a witch.Growing up I watched shows like Sabrina and Charmed and movies like The Craft and Practical Magic and I so badly wanted to be like those girls.

The 12 year old inside of me couldn’t pass up the opportunity to stop in Salem.

We parked right near the Witch House (which was unfortunately closed by the time we got there) and explored the very small downtown. If I could go back in time I would have skipped driving through Boston and tried to make before 5pm to tour the Witch House. That’s what you get for being spontaneous though.

I have researched Salem around October and it truly comes alive for tourism around Halloween season. But even in the dead of summer, Salem knows how to optimize on its history of witchcraft. There are a bunch of shops and restaurants catering to a little hocus pocus.

Booking a last minute hotel on day one.

When we started our road trip from New York to Maine, we decided to be flexible on where we ended our first night. I know that city traffic can be unreliable and that we wanted to take our time on the road so we didn’t know where we would end up. If you’re like me this may make you a little anxious. I encourage you to try and go with the flow anyway and see what happens.

Leaving Salem, we set our GPS to Portsmouth, NH, a little town right outside the border to Maine. At this point, I recommend taking the most direct route to Portsmouth. If you’re not too tired, keep driving straight through to Old Orchard Beach. It’s only a few hours north of Salem.

We found out on the road that pet friendly accommodations get pretty booked solid. Keep that in mind if you’re traveling with your dog. We ended up at a little pet friendly roadside Ramada Inn for the night not far from Old Orchard Beach. Of course if you’re not traveling with a pet, accommodations will be easier to find.

All Ramada Inn’s are pet friendly though and the hotel was perfect for a good night sleep and a shower. We stayed right off the highway in Saco. We got a couple bottles of wine and had a pizza delivered to our hotel room. I couldn’t have asked for a better first night on the road.

Day Two: Start in Old Orchard Beach

One of the only truly beach towns I encountered on our road trip from New York to Maine was Old Orchard Beach. This is a great spot to kick off day two of your road trip. It is like a teeny tiny Coney Island but with better weather and a nicer beach.

Get up as early as you can on day two and explore this beach town for a couple hours. Keep in mind if you are traveling with a pet that the beach is only dog friendly outside the hours of 10 am and 5 pm.

The pier doesn’t open until 11 am but there were plenty of shops and restaurants open on Old Orchard Street. During July and August, the theme park rides open at 11 am on weekends and noon during the week. Make sure to grab breakfast and some coffee at Green Mountain before you get back on the road.

Exploring Portland’s Head Light House

There is no shortage of Light Houses to explore on the east coast and Maine has some of the best. From Old Orchard Beach, you’ll want to head towards the Portland Head Light house in Cape Elizabeth. This is one of the most popular light houses in Maine.

I would give yourself at least an hour or two to explore the area around this beautiful attraction. There are picnic tables set up and food vendors if you want lunch with a view. We we were holding out for lobster in Portland though so we just wandered the grounds.

The only thing you have to pay for here is parking which is $7/hr with a 2 hour minimum. There is an adorable little gift shop to check out as well. And yes you can bring your dog here too as long as they are leashed at all times. Who knew Maine was SO dog friendly? Maybe everybody did but me.

Day Two Continued: Portland, Maine

You’re not far from downtown Portland once you leave here. Stop through for lunch and maybe even a trolly ride if you’re not traveling with your dog. I often travel to towns that I just automatically know I could live in and Portland is one of those towns.

In hindsight Portland would have been a great place to stop if I could have added another day to the trip. Something to keep in mind if your time is flexible. I am definitely planning to come back and spend more time in Portland.

Marshall Point Lighthouse

The Marshall Point Lighthouse was my favorite stop on our road trip from New York to Maine. You definitely have to go out of your way to get here but boy is it worth it. Yes it’s small and it’s located in an extremely secluded area in Port Clyde. But please don’t let that convince you to skip it.

Why did I love this lighthouse so much? It may have been because it is also dog friendly. Or maybe it’s because the weather was so perfect, or there was nobody there. (We arrived around 4pm.) Perhaps it was because the narrow bridge leading up to the lighthouse with the perfect Maine coast draped behind it is one of the most breathtakingly beautiful things I have ever seen. It’s probably all of the above.

Whatever you do, please please please do not skip this lighthouse.

Rockland, Maine: The lobster capital of the world.

Of course when I think of a road trip in Maine I think of fresh and delicious seafood. I have been a vegetarian for a little less than a year. It only seems to be a challenge though when I’m in a new city and want to experience it fully. Food is such a big part of a destination.

So I recently decided that I would allow myself to indulge in the local cuisine whenever I’m traveling. For these five days, I allowed myself to overload on fresh fish. There are endless places to stop along the road to have insanely fresh and delicious seafood.

Everyone knows that Maine is known for its lobster. So of course your road trip isn’t complete without a stop in Rockland, the lobster capital of the world. I forbid you to leave the state without trying a lobster roll in Rockland.

At this point in the road trip, I recommend staying on the the US Coastal Route 1 as much as possible. It lead us through some really cute coastal towns like Camden, Bath and a bunch of others that I can’t wait to explore on our next trip. Just making it through the towns and weaving in and out of the coast made for a very scenic route on our second day.

Ending Day Two: Where to Stay Near Acadia National Park

I knew when we started planning our trip that I wanted to go as far north as Bar Harbor. I also wanted to stay somewhere for a few nights that was secluded and scenic. We ended up booking a two night stay at the Lookout B&B in Brooklin, Maine, about an hour outside of Bar Harbor and Acadia National Park.

The property is nestled within the peninsula, right on the coast and offers an extreme decompression from New York City life. We rented out the property’s one bedroom Owenta Cabin in the middle of our trip. This B&B is great for anyone who really wants to have a quiet and relaxing stay, free of any distractions.

The cabin has no TV and A/C, which was a little terrifying at first but ended up being a blessing. The weather in Maine is pretty perfect but if it were any hotter I would have wanted a fan. The main house has WIFI but it does not reach to the cabin so it really does give you the opportunity to unplug.

The restaurant in the main house has incredible reviews. Unfortunately we arrived too late on our Sunday night stay to have dinner there and it’s closed on Mondays so we weren’t able to try it out. We did make use of the BBQ and fully equipped kitchen in our cabin and made dinner on our last night.

I would recommend this cabin for anyone willing to really be “away from it all.” The views are stunning and the atmosphere is peaceful. It’s a good location to get to and from Bar Harbor easily.

Day Three: Bar Harbor and Acadia National Park

Bar Harbor was by far the cutest place we visited on our trip. It’s a very small town right next to Acadia National Park that serves as a good place to kick off a day of hiking in the park. There are plenty of things to do in this little port town including boat rides and plenty of seafood to indulge in.

Our B&B was about an hour drive to Bar Harbor, which is further away than I would normally like to stay. But I didn’t feel like I was missing out on anything by not spending the night closer to the city. I’ll probably go back and spend a few days in Bar Harbor to see what the nightlife is like. Or even just to walk by the water at sunset.

Acadia National Park

I wish I were more outdoorsy because I love being in nature. But I have an irrational fear of anything that crawls, or flies, or slithers. I still try to enjoy national parks whenever I get the opportunity though. Even if you’ll probably never find me on a week long trek in the mountains.

Acadia National Park offers something for whatever your outdoor style is. If you don’t want to deal with parking they have roads that loop through the park with lookout points. But I recommend getting a parking pass ($30 for 7 days) and exploring a few of the trails.

Cadillac mountain is a great place to start your day as it is the highest point on the Eastern coast. We parked at the summit of this mountain and spent some time on the South Ridge trail. The trail ended up being a little too steep for our 12 year old dog so we didn’t make it all the way down. Who can carry a 65 pound pit bull up a mountain?

Whatever your taste is, there’s countless to explore at Acadia National Park and of course all the trails are dog friendly.

Day Four: Relaxing at the Colony Hotel in Kennebunkport

My real “vacation” started the second I was handed a glass of sparkling rose at the front desk of the Colony Hotel in Kennebunkport. This hotel is pure paradise right on the coast with exceptional service and gorgeous surroundings.

The fact that a hotel this nice is also pet friendly was completely shocking to me, but I won’t question it. I spent the better part of my last full day on vacation at the pool with a practically bottomless glass of rose. We didn’t even leave the hotel or go back to the room for dinner. We just moved right from our lawn chair to the pet friendly restaurant patio.

The hotel sits right above a private beach and includes a small putting course and a pool with bar service and padded lounge chairs. The pool area is dog friendly however dogs are not allowed in the actual pool. I think the only person who enjoyed this hotel more than me was Chewy.

Day Five: Head back home to New York City

The drive back home from Kennebunkport was just under five hours. That left time to take advantage of the Colony Hotel’s complimentary breakfast. It also left some time to lay by the pool and walk the private beach one last time before heading back to the city.

I spent day five mostly driving back to New York to beat the impending downpour heading for the northeast. I also wanted to get the rental car back to LaGuardia before rush hour. If you’re not in a hurry to get back to the city though there is opportunity to explore even more of Kennebunkport if you desire.

I look forward to spending more time in Kennebunkport next summer and actually exploring the town. But for the ending of this trip, I couldn’t be bothered to leave my little slice of paradise at the Colony Hotel.