Top 8 Stops on a Boston to Wells Road Trip [2024]

Looking to take a Boston to Wells road trip? You’re in the right place for a journey to create cherished memories!

This scenic drive from the bustling city of Boston to the serene coastal town of Wells, Maine, is more than just a route—it’s an adventure filled with diverse experiences. 

Along the way, you’ll discover charming New England towns, breathtaking coastal scenery, and an array of unique attractions. Wells, known for its beautiful beaches, historic sites, and inviting local cuisine, offers the perfect relaxing getaway. 

This road trip is an ideal blend of urban exploration and coastal tranquility, making it a must-do for anyone seeking a blend of history, nature, and relaxation.

I’ve partnered with my friend Laura from O Family Where Art Thou to share her experience on her Boston to Wells road trip.

Let’s jump in!

8 Stops on a Boston to Wells Road Trip

The best road from trip Boston will have multiple stops. Here are some of the best spots to make a stop on your Boston to Wells Road Trip.

1. Portsmouth, New Hampshire

First, set off from Boston and head north to Portsmouth, New Hampshire. This charming coastal town boasts a historic downtown area where you can stroll along Market Street. 

If you love seafood, you will be in paradise! Some of the best seafood spots in Portsmouth are Jumpin’ Jay’s Fish Cafe, Surf Restaurant, Row 34, and The Oar House.

When you plan a trip with multiple stops, take advantage of meal times. In Portsmouth, you can enjoy some fresh seafood during your Boston to Wells road trip. 

When you’re on a road trip to Portsmouth, taking a bike tour is super fun, especially on a sunny day. It’s a cool way to see all the neat and interesting spots in the city that you might miss in a car. You’ll get to ride around, learn some cool stuff, and have lots of fun exploring!

2. Kittery, Maine

As you cross the border into Maine, the next must-visit on the list is the delightful town of Kittery. Kittery will capture your heart and become a place you fondly remember. 

Have an absolute blast exploring the renowned Kittery Trading Post store, which offers an exciting array of outdoor gear and more. What made this stop particularly unforgettable was the unique dining experience at the restaurants on-site: hand-picking a lobster and savoring a freshly cooked, delectable lunch. 

Other restaurants where you can hand pick your lobster for a meal at the local seafood markets and restaurants that offer fresh, locally caught seafood. A popular spot is the Chauncey Creek Lobster Pier known for its scenic outdoor dining on a creek and a selection of live lobsters you can choose from. 

Another notable place is Robert’s Maine Grill. While it does not offer the hand-picking experience, Robert’s Maine Grill serves fresh and locally sourced lobsters and seafood dishes.

These places not only give you a taste of Maine’s famous lobsters but also offer a genuine New England seafood experience.

Kittery is truly a place that lives up to its reputation for outlet stores, bargain hunting, and superb seafood, making it a special addition to your drive from Boston to Maine.

3. York, Maine

Continue your coastal odyssey to York, Maine, a picturesque stop asking for a soak in its personality. The Nubble Lighthouse, full of history and perched along the rocky shores is very impressive. 

Venture further to the inviting Long Sands Beach, with its soft, golden sands. On a long road trip from Boston to Wells, walking along the beach will help you unwind and stretch your legs.

For a longer stop, visit the family-friendly zoo, York’s Wild Kingdom. York’s Wild Kingdom uniquely combines a zoo with an amusement park, offering interactive and educational experiences. 

It’s particularly renowned for its butterfly kingdom, allowing visitors to observe various butterflies up close. This blend of wildlife interaction and fun rides makes it a standout destination for all ages.

4. Ogunquit, Maine

Ogunquit, celebrated for its enchanting Marginal Way, is full of personality. Although Wells awaits just around the corner, you can’t resist a stop in Ogunquit. You won’t regret it! It may be hard to plan multiple stops on a road trip but slowing down and enjoying the journey is half the victory. 

Relish a lovely seaside lunch by the tranquil sailboats in Ogunquit Bay. The best price and experience we had with lobster in Ogunquit is at the Footbridge Lobster Restaurant.

Strolling along Marginal Way was a breeze for our family of five, offering us an unforgettable taste of the Maine coastline. 

This scenic coastal cliff path treated us to awe-inspiring views of the vast Atlantic Ocean. The city of Ogunquit added to our delight with its array of excellent dining options and its charming, welcoming character. 

For a thorough visit and a local guide’s insight, take a private day tour in Ogunquit. 

5. Wells, Maine

Once you reach Wells, it’s time for some fun! We personally stayed there for two weeks at a local RV campground, called Thousand Trails Moody Beach. 

Wells, Maine, a charming coastal town, offers a variety of activities for visitors. Known for its beautiful beaches like Wells Beach and Drakes Island Beach, it’s perfect for sunbathing, swimming, and beachcombing. 

Nature enthusiasts can explore the Rachel Carson National Wildlife Refuge. It offers a serene escape into nature, where one can immerse in the diverse ecosystems of coastal Maine. 

The refuge is also ideal for birdwatching, with a variety of migratory birds, and for enjoying peaceful walks along well-maintained trails through marshes and woodlands.

For history buffs, the Wells Reserve at Laudholm offers historical insights along with natural beauty. 

Antique lovers will enjoy the town’s numerous antique shops. Seasonal whale watching and deep-sea fishing are also popular.

Additionally, Wells’ proximity to other quaint towns like Ogunquit and Kennebunkport expands the possibilities for dining, shopping, and cultural experiences.

You can also visit the Wells Reserve at Laudholm Farm, a beautiful coastal nature spot.

One of the biggest draws in Wells is Wells Beach, which is a bit different from our Florida beaches, but the kids loved it.

For example, the beaches in Wells are known for their rugged New England charm, featuring cooler Atlantic waters, rocky shores, and tranquil settings, ideal for quiet beach walks and nature viewing.

Whereas, Clearwater, Florida’s beaches (where we are from) boast warm Gulf waters, expansive stretches of soft white sand, and a vibrant, lively atmosphere, making them popular for swimming, sunbathing, and water sports.

6. Old Orchard Beach, Maine

Old Orchard Beach is a resort town and a must-see on your way to see more of Maine. It is a hub of activity, offering amusement rides, games, and delicious treats. 

With 7 miles of soft sandy shores, it’s a perfect spot for beachcombing, building sandcastles, and enjoying the ocean’s refreshing waters such as renting stand-up paddle boards or kayaks.

The lively atmosphere is enhanced by live entertainment and a variety of local eateries serving up classic beachside fare. 

Whether you’re seeking thrilling rides, relaxation by the sea, or a mix of both, Old Orchard Beach combines classic charm and a vibrant atmosphere for a memorable family stop on your Boston to Wells road trip.

7. Portland, Maine

Take a little side adventure and check out Portland, Maine – it’s the biggest city in the state and has so much to offer!

This city on the harbor reminds me a lot of my Florida stomping grounds in Tampa like Tarpon Springs: lots of sailboats, it’s a walkable city with a special blend of high-rise buildings and nature. 

Portland is an incredible hidden gem, especially hiking at Mackworth Island. The trail is awesome, and you can see many cool things in nature, like the stunning views of Casco Bay and a Fairy Village, where visitors can create tiny natural houses. 

The island also offers diverse birdwatching, picturesque shores, and a rich cultural connection to the local Native American community.

After our hike, we explored the boardwalk by the water with amazing places to eat right downtown! Grab delicious hamburgers at Elevation Burger and donuts at The Holy Donut, which are super yummy! 

You can also make your time in Portland even sweeter by booking a donut tasting walking tour! Explore with a personal guide.

Make your day even more exciting and finish it with a fantastic Maine Narrow Gauge Railroad ride. Portland is full of surprises and can make your road trip extra special!

8. Freeport, Maine

Freeport, Maine is an awesome place to add to your Boston to Wells road trip. It’s famous for two big things: shopping and outdoor fun. One especially cool spot in Freeport is the L.L.Bean flagship store. 

If you love being outdoors and going on adventures, this store is like a dream come true! They have all sorts of gear and stuff for outdoor enthusiasts. 

Check out Wolfe’s Neck Woods State Park if shopping isn’t your thing. You can go hiking and even try kayaking in the water. Plus, you can hop on a boat and take a tour to see the scenic views. 

Freeport is super friendly, and you enjoy shopping and playing outside. It’s a great place for a little adventure on your way back to Boston or a stop when you’re visiting Wells. 

How long is a Boston to Wells road trip? 

A road trip from Boston to Wells can take around 1.5 to 2 hours, but it depends on how many stops you make along the way and the traffic.

If you’re in a hurry, it can be quicker, but it’s more fun to take your time and explore cool places like Portsmouth, Kittery, York, and Ogunquit. 

The Boston to Wells road trip can be a day trip or span several days with you enjoying all the fantastic sights and adventures along the route. It’s not just about the destination; it’s about the journey and all the memories you create!

Where to stay on a Boston to Wells road trip?

Even though this Boston to Wells road trip is only a short drive, you can appreciate the scenic route and take a couple of days to enjoy the nearby cities. 

Hampton Inn & Suites Kittery

It’s best to stop in Portsmouth for a delicious late lunch then head to Kittery for the evening. Book a stay at the Hampton Inn & Suites to rest on your Boston to Wells road trip.

Anchorage by the Sea (Ogunquit)

Enjoy your free breakfast then head over to the local shops. Afterward, you can head to York for a tour of the lighthouse or calm beaches.

You will still have time to drive to Ogunquit where Marginal Way is a must at sunset. Spend the night at this oceanfront resort (you may be tempted to extend your stay once you see the amenities).

Hampton Inn Portland Downtown Waterfront

The next morning, Wells is only a short drive down the road. If you venture a little further and want to stay in Portland, a great stay right in the heart of downtown is at the Hampton Inn Portland Downtown Waterfront.

What is the best month to travel to Maine? 

The best time to visit Maine is during the summer months, especially in July and August when the weather is warm, and everything is in full bloom. You can go to the beaches, hike, and enjoy outdoor activities. 

But if you like colorful leaves and cooler weather, then September and October, known as the fall season, are great. The trees change into beautiful reds and yellows, and it’s lovely. Remember, winter can be super cold and snowy, so be prepared for cooler weather. 

Is the Drive from Boston to Maine pretty? 

Yes, the drive from Boston to Maine is super pretty! You get to see a lot of cool stuff along the way. You can catch glimpses of the ocean, green forests, and cute towns. 

It’s especially beautiful in the summer and fall. During the summer, you can enjoy the blue skies and the sparkling water. In the fall, the trees turn all sorts of amazing colors, like red, orange, and yellow. 

Whether you’re looking at the coastline or the forests, the drive from Boston to Maine is like a picture book come to life. You’ll have a great time seeing the sights!

Final thoughts: Boston to Wells Road Trip

Our road trip from Boston to Wells was incredible and a forever memory for our family. Every place we stopped at, from the cool streets of Portsmouth to the sunny beaches of Old Orchard Beach, was super special and fun. 

Maine was so beautiful with its nature and friendly towns, and Wells was the best part where we laughed a lot and had a great time. If you’re thinking about taking this road trip, you definitely should! 

It’s a big thumbs up from me – it’s so much fun!

Ready to explore the New England coast? Check out these posts!

Author Bio: Laura Mendenhall is a full-time nomad as she explores the country in an RV called “The Mendenhauler” with her husband, three kids, and a dog. When she’s not exploring caves, historic monuments, or farms, Laura enjoys writing, cooking, and laughing at corny jokes (they get her every time). She is the author of a best-selling book, Love Fast Live Slow, and the creator of the family travel blog, O Family, Where Art Thou.

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