Boston to Portland, Maine: 15 destinations that make the ultimate road trip

When you think of New England, what comes to mind? Small, red fishing shacks, waves crashing on rocky shores, fresh lobster rolls? The region is all of this and so much more. 

It’s history — think the Salem Witch Museum and dozens of iconic lighthouses. It’s food — clam chowder and craft beer spots galore. It’s nature, too — parks for hiking and beaches for relaxing. Sounds enticing, right?

Step out of your routine and step into the postcard-perfect landscape of New England with an iconic road trip from Boston, Massachusetts to Portland, Maine. Map out any, or all, of the 15 destinations below while planning your route.

And finally, reserve a Greenvans 15-passenger van rental in Boston, MA to guarantee the utmost comfort on the road and set off on your adventure! 

1. Salem, Massachusetts

A visit to the site of the infamous witch trials is our first, highly recommended stop on a drive from Boston to Portland, Maine. Dive into one of the country’s eeriest epochs at the Salem Witch Museum before shaking it off at the House of Seven Gables, the historic mansion made famous by American author Nathanial Hawthorne. You’re sure to enjoy a few hours scoping out Salem’s bustling waterfront brimming with public art, fresh lobster, pubs, and live music venues. 

Capitalize on a van rental by expanding the radius of your road trip, that way you can explore a few more New England winter getaways just a few hours from Boston!

Road trip tip: Park in central Salem to easily walk between attractions.

Distance from Boston: 16 miles

Distance to Portland: 95 miles

Source: Fine Art America

2. Rockport, Massachusetts

For a quintessential New England photo opportunity, plan a stop in Rockport. This classic seaside town is home to Motif No. 1, a widely painted and photographed red fishing shack located at the end of Bradley Wharf. 

After a group photo head to Bearskin Neck, a peninsula-like neighborhood that sits directly on the water. Get lost for hours wandering the narrow, cottage-lined streets teeming with art galleries, craft boutiques, and seafood restaurants where you can fuel up before driving to your next stop.

Road trip tip: Drive along Route 128 for coastal views.

Distance from Boston: 39 miles

Distance to Portland: 100 miles

Source: Cape Ann Vacations

3. Gloucester, Massachusetts

The enchanting town of Gloucester should definitely be on everyone’s travel radar during a Boston to Maine road trip. The architecture is quaint, the views are breathtaking, and the community is known to be welcoming to its visitors. From landmarks like the Fishermen’s Memorial to picturesque beaches and outstanding clam chowder, everyone will be happy to spend a day here.

Road trip tip: Drive along the scenic Cape Ann coastline; find street parking near the waterfront.

Distance from Boston: 35 miles

Distance to Portland: 99 miles

Source: Good Morning Gloucester

4. Newburyport, Massachusetts

Another characteristic New England town to check out is Newburyport. Wander the pedestrian-friendly downtown, known for its well-preserved red-brick buildings housing a mix of boutique shops, art galleries, restaurants, and cafes. Check out some cool artifacts from famous shipwrecks at the Custom House Maritime Museum. 

A perk about renting a van for your road trip is its spaciousness. That way, bringing along towels, chairs, and other beach necessities is no big deal, enabling you to take a short drive across the bridge to the sandy shores of Plum Island Beach. Relax for a few hours in the sun or explore the wildlife refuge at Parker River.

Road trip tip: Follow the scenic Merrimack River route; park near the downtown area for easy exploration.

Distance from Boston: 38 miles

Distance to Portland: 72 miles

Source: TripSavvy

5. Portsmouth, New Hampshire

Renowned for a unique mix of architectural styles, Portsmouth is a visually appealing town with a bustling historic heart. Market Square overflows with local shops, restaurants, and interesting museums like Strawbery Banke, making it a great place to spend an afternoon. Wrap up a lovely day trip to Portsmouth with a stroll through the vibrant gardens and waterfront in Prescott Park. The city also hosts a variety of festivals throughout the year celebrating everything from wine to pumpkins, so be sure to check the schedule while planning your road trip from Boston to Portland, Maine. 

Want to extend your stay or come back to Portsmouth later? Discover more to do on your Portsmouth road trip with our guide.

Road trip tip: Enter Portsmouth via the scenic I-95 bridge.

Distance from Boston: 56 miles

Distance to Portland: 52 miles

Source: NH Magazine

6. Kittery, Maine

Looking for Maine’s oldest town? Take a quick stop in Kittery, a destination that seamlessly blends old 17th-century houses with a new, pulsing downtown called Foreside. There is also much nature to be discovered in Kittery, so check out the many kayaking, boating, and wildlife-watching options in places like Pepperrell Cove. If shopping is your preferred sport, you won’t be disappointed with a visit to the famous Kittery Outlets.

The Portsmouth Naval Shipyard is a short drive away from Kittery. Take a guided tour to learn about the shipbuilding industry and see submarines and other naval vessels being repaired.

Road trip tip: Take I-95 for a direct route; use designated outlet parking and explore the area’s historic sites and dining options nearby.

Distance from Boston: 59 miles 

Distance to Portland: 50 miles

Source: Visit Maine

7. York, Maine

Families road-tripping together will especially enjoy a stop in York, a classic seaside village that’s home to Nubble Lighthouse, one of the most photographed lighthouses in the entire country (and a fantastic photo opp). York’s rocky beaches are a great location to enjoy a picnic after a visit to Wild Kingdom amusement park, so make sure to pack lunch and a big blanket. 

If you want to extend your trip for more lighthouse views, check out these New England lighthouses.

Road trip tip: Drive along Route 1A for ocean views; use public parking near Short Sands Beach.

Distance from Boston: 64 miles

Distance to Portland: 44 miles

Source: Stanton Champion

8. Ogunquit, Maine

With its charming small-town atmosphere, Ogunquit is a lovely stop to enjoy views of the Atlantic Ocean and beautiful New England architecture. Take a walk along Marginal Way, a mile-long coastal path that shows off the landscape’s rugged cliffs, sandy beaches, and little fishing boats. Another great opportunity to stretch your legs is the three-mile stretch of Ogunquit Beach. 

For art lovers, check out local galleries and Broadway reproductions at the historic Ogunquit Playhouse, all in the center of town.

Road trip tip: Follow Shore Road for a picturesque drive; park in the central lot for beach access.

Distance from Boston: 71 miles

Distance to Portland: 38 miles

Source: Visit The USA

9. The Kennebunks (Kennebunk and Kennebunkport), Maine

The Kennebunks are two neighboring towns, with Kennebunkport located directly on the shoreline. Lively Dock Square is a popular stop on a road trip from Boston to Portland, Maine, where visitors can shop in boutiques or dine on fresh-caught fish. For something quieter, Kennebunk is home to beautiful architecture — one of its landmarks is called The Wedding Cake House — and calm but picturesque beaches.  

Ocean Avenue is a one-mile coastal drive with views of rugged cliffs and classic lighthouses that shouldn’t be missed. 

Road trip tip: Enjoy the scenic drive on Route 9; park near Dock Square for walking tours.

Distance from Boston: 84 miles

Distance to Portland: 28 miles


10. Biddeford and Saco, Maine

Another fun stop on a Boston to Maine road trip is the neighboring towns of Biddeford and Saco. The pair offer a complimentary experience, with Biddeford showcasing historic mills repurposed into eclectic mixed-use spaces, including restaurants, craft breweries, art galleries, and shops. 

Saco, on the other hand, offers a more laid-back atmosphere with its charming tree-lined streets and colonial neighborhoods. Nature enthusiasts will enjoy hiking, biking, and picnicking in Ferry Beach State Park, a 10-minute drive away.

Road trip tip: Use Route 1 for a direct route; explore the mills and downtown areas on foot.

Distance from Boston: 96 miles

Distance to Portland: 18 miles

11. Old Orchard Beach, Maine

To avoid crowds, travel during New England’s off-season, notably September, an ideal time of year to visit Old Orchard Beach. Relax on its long stretch of shoreline before an evening on the lively pier, which juts out into the Atlantic Ocean and is adorned with shops, restaurants, and arcades. For the young and the young at heart, Palace Playland is an amusement park uniquely located right on the beach, featuring rides and games for all ages.

Road trip tip: Take the Old Orchard Beach exit off I-95; parking is available near the beach.

Distance from Boston: 102 miles

Distance to Portland: 19 miles

Source: Visit Maine

12. Scarborough, Maine

How do white sandy beaches, picturesque rocky promontories, and a quaint New England ambiance sound to you? If your interest has been piqued, stop in Scarborough. The town offers a variety of activities for visitors to enjoy, including swimming, sunbathing, and strolling along the shore. Scarborough Marsh is renowned for being Maine’s largest salt marsh and home to abundant wildlife, especially birds. Rent canoes or kayaks for a unique perspective of this ecological gem.

Road trip tip: Coastal Route 1 offers a scenic drive; park at the Eastern Trail access points.

Distance from Boston: 107 miles

Distance to Portland: 7 miles

13. Cape Elizabeth, Maine

You’ve nearly arrived at the final destination on your road trip from Boston to Portland, Maine! Don’t skip a visit to Cape Elizabeth, where you can explore the lush landscapes and walking trails at Fort Williams Park. 

The star attraction within the park is Portland Head Light, the oldest lighthouse in Maine. Photographers will find it particularly enchanting, as the combination of rugged coastlines, crashing waves, and the lighthouse makes for gorgeous photo opportunities.

Road trip tip: Drive through Shore Road for stunning coastal scenery; park at Fort Williams for the lighthouse.

Distance from Boston: 118 miles

Distance to Portland: 9 miles

14. South Portland, Maine

Located on a peninsula across from Portland, South Portland has a thriving waterfront area with views of Casco Bay and Portland Head Light. It’s got a diverse culinary scene showcasing fresh lobster rolls and that famous New England clam chowder. Wash it all down with South Portland’s most popular beverage, the local craft beer.

Take a stroll along the Greenbelt Walkway, a scenic trail that meanders through the city. Stop by Bug Light Park to snap a picture of the historic lighthouse uniquely shaped like a bugle. 

Road trip tip: Cross Casco Bay Bridge for views; park in the Mill Creek Park area for walkability.

Distance from Boston: 113 miles

Distance to Portland: 3 miles

Source: Downeast Magazine

15. Portland, Maine — Eastern Promenade 

You’ve officially reached the final destination of your Boston to Maine road trip. First thing first, stretch your legs with a walk through the trails of the Eastern Promenade, enjoying panoramic views of Casco Bay. It’s also home to East End Beach, where you can relax and soak up the sun before exploring the Old Port District for its lively bars, restaurants, and shops. The food scene in Portland is hopping, with delicious cuisine everywhere you turn. Check out the Portland Farmers’ Market for local produce, artisanal products, and food vendors. 

Road trip tip: Enjoy the views along the Eastern Promenade.

Distance from Boston: 112 miles

Distance to Portland: 0 miles! You made it!

Common questions about driving from Boston to Portland, Maine

Embarking on a road trip is an exciting endeavor that’s sure to spark plenty of curiosity. Below is a list of the most common questions and answers about driving from Boston to Portland, Maine. 

How long is the drive from Boston to Portland?

The drive from Boston to Portland is 112 miles long and takes approximately 1 hour and 40 minutes without stopping. 

While not very long, there are so many beautiful places to see along the way, we encourage travelers to extend their road trip over several days. This allows enough time to soak in that classic New England landscape while also exploring its charming seaside towns. 

Is Portland, Maine worth visiting?

Portland, Maine is definitely worth visiting! There are so many reasons to discover Portland, like its thriving art scene, award-winning dining, rich history, and surrounding natural beauty. From whale watching to craft breweries, and museums to lighthouses, visitors are regularly captivated by Portland’s range of unique activities and vibrant atmosphere. 

What is the best way to get from Boston to Portland, Maine?

The best way to get from Boston to Portland, Maine is in a Greenvans van rental. Renting with Greenvans guarantees:

  • Freedom to enjoy the landscape on your terms while checking out multiple towns on your Boston to Maine road trip.
  • A modern, well-maintained vehicle showcasing Apple Carplay, Android Auto, Sirius XM radio, and USB ports in every row.
  • Space to comfortably fit your family, your dog, your suitcases, and any extras you might need from hiking gear to picnic essentials. 
  • A team of expert road trippers and crisis managers by your side before, during, and after your trip.

Load up your van and head off to Portland! 

A journey along New England’s coast is truly one of the USA’s most iconic road trips. The ride from Boston to Portland, Maine is full of picture-perfect coastal villages where you can stop for fresh lobster rolls and strolls along the rocky coastline. From the beach to breweries, and lighthouses to amusement parks, the memories you create on this trip will stand out for years to come. 

Whether you decide to share this experience with your family or your closest friends, Greenvans is here to make sure your adventure is smooth and comfortable. Rent a 15-passenger from Boston and hit the road for Portland!


The quality & service you’re looking for is right here.