Boston to Maine Road Trip: The Complete Itinerary (2026)

Boston to Maine: the classic mini east coast road trip. As far as getaways from Boston go, it’s an easy, breezy state to visit in under a few hours. And one that rewards you differently depending on how far north you’re willing to go. When I was growing up, we used to go to Maine all the time for family vacations. From Bar Harbor and Sunday River to Saco and Portland, I enjoyed locations up and down the coast. This itinerary is my attempt to map out the best version of that trip for people who want more than a quick overnight, with the option to tailor it to a long weekend or a full week depending on how much time you have.

The route runs north on I-95 from Boston through southern New Hampshire and into Maine, stopping at Ogunquit, Kennebunkport, Portland, and, if you have the time, Camden on the mid-coast. You can hop in the car or take the train for part of it. Either way, start anywhere on Route 95 and head north.

The Route at a Glance

This itinerary is designed as a flexible 5-7 day road trip, but it scales down easily. Here’s how to think about the length:

Weekend (2-3 days): Boston to Ogunquit and back, with a Portland stop on the return. Five days: The full southern Maine loop: Ogunquit, Kennebunkport, Portland, and back. A week or more: Add Camden for the mid-coast experience, and you have one of the best road trips in New England.

The full drive from Boston to Camden is about 2.5 hours without stops. Every stop along the way adds its own world, and none of them feel rushed if you give them at least a night.

Before You Leave: Starting in Boston

Before heading north, it’s worth spending at least one night in the city if you haven’t already. I’ve spent so many fun nights out in Boston and brought friends from all over the world to stay overnight so we could really let loose. It’s an ideal launching pad for a road trip, especially if people are flying in from different places.

For a South End base, StayPineapple is a fun and comfortable option right in the neighborhood. It’s quirky with pineapple-themed decor, plush robes, and connected to the Trophy Room for cocktails and bar bites downstairs. The South End puts you walking distance from some of the best restaurants in the city: The Beehive for brunch and live music, Barcelona Wine Bar for tapas and a good red wine, and Kaia for elevated Mediterranean. After dinner, pop into Madeleine’s candy shop on the same strip for a pick-and-mix bag of Swedish-style treats.

If you want the Seaport instead (closer to the highway north and a bit more modern energy) the Hampton Inn Seaport is clean and well-located, and the Omni Seaport is worth it for the free parking package if you’re already in your car.

READ MORE: Girls Weekend in Boston

READ MORE: Best Things to Do in Boston

New Hampshire: Worth a Stop

The drive north takes you straight through New Hampshire on I-95. It’s only a sliver of the state coastline, but it’s worth a pause. Two options depending on your mood:

If you want to stay coastal, Portsmouth is a lovely lunch stop: a small, walkable city with great independent restaurants and a waterfront that punches well above its size. It’s right off the highway and easy to dip in and out of.

ariel shot cranmore noth conway new hampshire

If you want to go inland for mountain views and a ski-town vibe, North Conway is a detour worth making. But, note it takes you off the coastal route onto Route 16, so plan for it as a deliberate side trip rather than a quick stop. It’s especially good in fall foliage season and winter.

One more thing: don’t skip the New Hampshire liquor stores at the state border. No tax! It’s a New England road trip tradition! I’m also NOT saying you can’t buy fireworks in Massachusetts, but you can buy them in New Hampshire and Maine.

Days 1-2: Ogunquit and the Cliff House

The first major stop on any Boston to Maine road trip should be Ogunquit. It’s a gorgeous stretch of southern Maine coastline about two hours from Boston. Ogunquit Beach is one of the finest on the coast, with a long sandy stretch and a tidal river perfect for kayaking. The town itself has a good mix of restaurants, galleries, and the famous Marginal Way: a mile-long cliffside walking path along the ocean that’s worth doing at any time of year.

cliff house ogunquit main lobby and lounge with cliff views

The Cliff House

Have you ever entered a grand ballroom? Where the ceilings are high like a palace, and there’s decadent detail in every corner? The Cliff House in Ogunquit offers just this with a modern Maine twist.

While our beautiful room was cozy and decked out with traditional nautical decor, the real draw was the grand entrance of the hotel. Its history dates back to the late 1800s, and it has been a breathtaking place of tranquility ever since. Check in at the main lobby area, then descend down the staircase to be greeted with sweeping, floor-to-ceiling views of the cliffs and ocean waves. Maine does rugged seascape like no other, and the Cliff House has managed to bottle it up all in one panoramic vista.

eileen in a mirror at the cliff house spa in maine

The Cliff House has everything you need to stay put for a night or two, with indoor and outdoor pools, an outdoor heated hot tub that looks especially good against a winter snowscape, and a spa with proper treatments and big robes to wander in. The Tiller Restaurant does lobster dishes year-round, and the dessert of homemade cookies and blueberry ice cream was the highlight of our stay. Take your nightcap out to the lounge area for live acoustic guitar on weekends.

Check out some Ogunquit Maine tours and activities

Days 2-3: Kennebunkport

About 20 minutes north of Ogunquit, Kennebunkport is one of those New England towns that earns its reputation completely. It’s the kind of place where you park the car and spend the rest of the day on foot, which is a nice relaxed pace for a road trip that’s been moving since Boston.

Dock Square is the heart of things. Lined with independent shops, galleries, and restaurants, it spills down to the bridge between Kennebunkport and Lower Village where people routinely eat lobster rolls perched on the railing and watch the boats pass underneath. There’s nothing like the smell of salty air on a sunny afternoon in Maine.

Colony Beach is the local favorite for getting in the water. It’s public, no parking pass required, with that classic Maine rocky-jetty-meets-sand setup and tide pools worth exploring at low tide.

For a lobster roll, Mabel’s Lobster Claw has been an institution here for decades. For dinner, Earth at Hidden Pond is the splurge: locally sourced, candlelit barn setting, worth it. The Captain Lord Mansion is the classic bed and breakfast stay right in the village, with fireplaces in most rooms and a full breakfast every morning.

Here’s some great Kennebunkport whale watching and watersport tours!

Days 3-4: Portland

Portland is less than an hour north of Kennebunkport and is one of the best small cities in America for a weekend. I’ve been back multiple times and find something new every trip. It sits on a peninsula jutting into the harbor, walkable, with extraordinary seafood and a waterfront never more than a few blocks away.

Where to Stay

For groups, the Aloft Portland Downtown Waterfront is the best combination of space, amenities, and a great lobby bar. Parking is on-site, rooms are sunny and spacious, and the location puts you within walking distance of almost everything. Pets welcome, adjoining rooms available.

For something with more boutique energy and the best rooftop bar in Portland, the Canopy by Hilton is right in the old part of town. The Luna Rooftop Bar is already the go-to gathering spot: Greek goddess-inspired cocktails, tapa-style plates, and city views that earn the detour. The hotel also offers bike rentals, which comes in handy Saturday morning. The Press Hotel is a third option, beautifully converted from a newspaper press building, great energy for a couple’s trip or girls trip stay.

Friday Evening

blyth and burrow portland cocktails oysters

Portland’s walkable core makes happy hour a wandering affair. Start at the Portland Hunt + Alpine Club for some of the most thoughtful cocktails in the city The Swedish meatballs are better than they have any right to be. Blyth & Burrows is next: inventive cocktails and some of the best oysters around. My husband once ordered a drink with clarified tom yum soup in it that immediately transported us back to Thailand. He ordered two! For late night, Taco Escobar is the local move: no frills, great margaritas, excellent tacos.

Saturday: The Promenade, the Lighthouse, and Dinner

A late morning stroll or bike ride along the Eastern Promenade is one of the best free things you can do in Portland. The two-mile paved path runs along the water, filled with couples, dogs, kids, and the general energy of a city that knows how to enjoy a Saturday. The same landscape architects behind Central Park and Boston Common designed this one. If the food trucks are out, don’t skip the Maine Maple Creemee Co. They have fresh maple soft serve with crumbled maple potato chips, which sounds strange and is genuinely unforgettable.

In the afternoon, drive about 15 minutes out to Portland Head Light on Cape Elizabeth, the oldest lighthouse in Maine, dating to the late 1700s, with craggy coastline that feels genuinely wild. Bring takeout from Bánh Appétit for a Vietnamese sandwich and eat it by the water.

For dinner, Scales is the move if you came to Portland for the seafood (which you should have). Seasonal menus, whole Branzino, mussels cooked in hard cider, exceptional artisan bread. A proper dinner.

Sunday: Breweries Before You Go

Portland has a remarkable density of excellent breweries for its size. Oxbow Blending and Bottling is the first stop, with aged and mixed fermentation beers with food on-site. Allagash is known across the country for good reason, though it’s a 15-minute drive from downtown. Just check the hours before going. Maine Craft Distilling is the non-beer option; their premixed cans are worth taking home.

Finish with lunch at Terlingua: part marketplace, part BBQ pit, part Mexican fare, entirely Portland. The back patio is wonderful, the tacos are excellent, and the tres leche cake is non-negotiable road trip sustenance.

Freeport: The Shopping Stop

Freeport sits between Portland and Brunswick and is worth a stop for one reason above all others: the L.L. Bean flagship store. Multiple buildings, a trout pond, walls of taxidermy, and a shopping experience that’s uniquely Maine. Other retailers have moved in around it (Patagonia, Fjallraven), and the Freeport Café nearby is worth a breakfast stop for the home fries alone. Don’t miss a beer and a brick oven pizza at the Maine Beer Company either. If you’re doing the full northern route, this is a natural break between Portland and Camden.

Days 5-6: Camden: The Mid-Coast Extension

If you have the time, do not skip Camden. About an hour and twenty minutes north of Portland, it’s where the road trip shifts from lively coastal city energy to something quieter and more distinctly Maine. I’ve been there in summer when it’s a relief from the heat further south, and in shoulder seasons when the light over Penobscot Bay is extraordinary. All year round works here.

Camden, Maine is one of my favorite new discoveries. It’s slightly smaller than Kennebunkport with a classic coastal town feel and just as much to experience.

Where to Stay

The Hartstone Inn & Hideaway is ideal for a cozy Camden stay. Only steps from the marina and the best restaurants in town, the inn is comprised of several refurbished homes with modern amenities that work well for couples, families, and small groups. Many suites have private entrances, some with jetted tubs and gas fireplaces, others with access to private terraces. Rooms come with fresh breakfast every morning, and there’s a coffee station open all day.

Our main meal at the inn was curated by Chef Dustin to feature local ingredients with a twist. Hartstone is known for its tasting menu, and the homemade clam chowder and seared tuna were both exceptional. The desserts were showstoppers.

If you stay three nights, the inn includes a complimentary sail through Penobscot Bay with Schooner Surprise, and that sail was the single best thing we did the whole trip. Pick up sandwiches from the Camden Deli before you board. The #39 Surprise sandwich and the homemade peanut butter cup are both mandatory.

In Town

Camden is easy to get your bearings in. Walk down Elm Street from the inn toward the water. You can grab a strong espresso at Zoot Coffee or a beer at Seadog Brewing Co., peek into Hundred Acres for local goods, and spend a leisurely morning along Camden Harbor Park. Watch the sailboats from the opposite side of the harbor, where you’ll find the Whistling Whale coffee shop and Barren’s Distillery. Round out the day with a happy hour at The View, overlooking the water and park.

Up on the Mountain

Camden is one of the rare coastal towns where you can hike a mountain and see the ocean from the summit. Mount Battie in Camden Hills State Park is an accessible hike with a serious payoff — panoramic views over Penobscot Bay and the harbor below. The drive to the summit is also an option. Either way, get up there.

Getting There: Drive vs. Train

By Car

The drive from Boston to Ogunquit is about two hours on I-95 North. From Ogunquit to Kennebunkport is 20 minutes. Kennebunkport to Portland is another 30. Portland to Camden is about 80 minutes. The full drive from Boston to Camden is roughly 2.5 hours without stops.

Here’s some options for car rentals to and from Boston with the best rates.

By Train

The Amtrak Downeaster runs from Boston’s North Station north through New Hampshire and into Maine, stopping at Wells (closest to Ogunquit, about 7 miles by taxi from the Cliff House), Portland, Freeport, and Brunswick. It’s a great option if you want to skip the drive: smooth, clean, and if you book ahead, comparable in price to gas. The train ends in Brunswick, so Camden still requires a car for the last stretch. A smart hybrid approach: train to Portland, rent a car there for the Camden leg, return the car and train back.

Best Time to Visit

cape elizabeth lighthouse with bahn mi sandwich in maine

Maine rewards you differently in every season.

Summer (July-August) is peak trave time. The beaches are warm, everything is open, lobster is at its best. Book well ahead though, especially in Kennebunkport and Camden.

Fall (late September through mid-October) is my favorite time to make this drive. Foliage along the coast and through New Hampshire is spectacular, crowds thin after Labor Day, and the light is extraordinary. If you can go in October, go in October.

Winter is underrated. The Cliff House with its outdoor hot tub against a snowy landscape is a genuinely wonderful thing, and the whole coast gets quiet in a good way. Camden Snow Bowl nearby is the only ski mountain in the US with ocean views.

Spring (May-June) brings wildflowers, the green coming back, and some of the best rates of the year. The water is still cold, but hiking and town-wandering are ideal.

Have the best time!