The Ultimate East Coast Road Trip: 5 States in 5 Days

While we Texans can drive 12 hours and still never leave the state, the east coast is blessed with the accessibility to see a lot in a short amount of time. If you’re looking to make a big dent in your USA bucket list and check off a number of new states, here are the shining gems and not-to-miss spots perfect for a spring, summer, or fall east coast road trip. This Maine to Boston itinerary has planes, trains, boats and trolleys, mountains and beaches, small towns and big cities, and is perfect for those without a million vacation days to burn.

Of course, if you have some flexibility, give yourself a few extra days to explore so you can see more. A bit of padding never hurts in case the weather doesn’t cooperate, but if time is tight, you’d be surprised just how much you can pack into a week. Without further ado, let’s hit the road, shall we?

Day 1: Maine 

Fly into Bar Harbor (10-minute drive) or Bangor (1 hour). Boston Logan has connections from each and grab a rental car.

For your first day, your home base for explorations will be Bar Harbor at the very tippy-top northeast corner of the US on the Atlantic Ocean before you cross the border to Canada. The gateway to Acadia National Park, this cobblestone beach town looks like it was straight out of a Hallmark movie with all the homes built before 1901 (I forget the east coast has much more history than the rest of the country), and water never gets above 56 degrees (the lobsters love it, the humans not so much). You’ll find almost no chain restaurants or shops so wander the streets, peruse the boutiques, indulge in your first lobster roll and cup of chowda, and watch the boats come in.

Don’t miss: Your nose will lead you to Ben and Bill’s Chocolate Emporium, which has wall after wall of truffles, fudge, and sweets galore. They boast over 100 flavors of ice cream, including lobster.

When you’re ready to hit the trails, Acadia National Park is a stunning recreational area. It is one of the smallest national parks in the country and the first national park east of Mississippi, yet one of busiest. Designed by the same architect as Central Park in NYC, it’s beautifully landscaped (albeit largely manmade). There are a few ways to explore via the self-drive car loop, the Island Explorer, the park’s free shuttle bus, and guided bus and trolley tours if you want to relax and take it all in. One of the most unique ways to see the sights is on one of the park’s carriage routes, available May through October.

Mount Desert is the most concentrated (read: popular) part of the park and what first-time visitors want to see, which is what the drive loop circles. You’ll hit three of the main attractions: Cadillac Mountain (note: you’ll need reservations to summit), Jordan Pond lake, restaurant and overlook, and Thunder Hole with its iconic pink granite cliffs and dramatic beaches. The park is open 24/7, so if you’re keen on avoiding the crowds or getting a bit of hiking in, consider coming offseason or off-hours.

Hit the Road: From there it’s a three-hour drive up the coast to Portland. But don’t miss the LL Bean flagship store, which is a fun stop and photo op if you need to stretch your legs.

Stop: Portland, Maine

Maine’s largest city, is home to less than 100,000 residents, still giving it that coveted small town, hyper-local feel. It’s artsy, eclectic, hipster, and charming, and the best way to explore is to wander. Head to the Old Port area, take in the waterfront sunsets, boutiques, and insane food scene. If you have time, get out on a boat (we loved the 100-year-old wooden schooners from Portland Schooner Co.), relax at Soakology (a foot spa and teahouse aka. what dreams are made of), eat your fill of seaside seafood, photograph the lighthouses, and marvel at the mega-mansions of Cape Elizabeth.

Overnight in Portland: The Press Hotel (Splurge), Black Elephant Hostel (Budget) 

Day 2: New Hampshire

Be sure to pack a jacket because the landscape is about to change dramatically – and we’re going from one extreme to another, the beach to the mountains. A 2-hour, 20-minute drive from Portland, Mount Washington is the highest peak on the east coast and home to the world’s worst weather, which is no joke as the wind regularly clocks in at 70-200 miles an hour (it’s so bad it’s actually where the military practices their extreme helicopter takeoffs).

But don’t let that scare you because the sights are worth it. Part of Appalachian Trail, Mount Washington is a popular hiking area, but the more fun way to summit is the Cog Railway. Passing through four eco-zones, the ride up feels like a long and slow ascending rollercoaster in brightly colored cars that looks a bit like a Disney train that takes about three hours round trip. If you’d rather stretch your legs, you can hike 3-7 miles uphill and take the train back down.

STOP: FLUME GORGE

We wanted to save our thighs as just 45 minutes away is the GORGE-ous (pun intended) Flume Gorge. An accessible 1.5-mile waterfall ravine, scoot along the boardwalks and take in greenery that looks like it’s straight out of Narnia.

 Overnight in New Hampshire: Conway is the largest ski town in the area with the most amenities, but there are tons of B&Bs dotted around the White Mountains (which is a bit of a deceiving name as the area is really quite green in summertime). Recommended hotels: Omni Mount Washington (Splurge), North Conway Grand Hotel (Midrange), Golden Gables Inn (Budget)

Day 3: Vermont

Today it’s off for more greenery in the rolling hills of Vermont. Known for cheese, ice cream, beer, cider, and farm to fork goodness, we’re spending the day eating our way through the Green Mountain State. Starting in Stowe, map out your spots along the Cheese Trail, taste one of the best apple cider donuts in the country at the Old Cider Mill (they also have hard cider flights and apple cider hot dogs if you’re so inclined), and snag a scoop at the original Ben & Jerry Factory in Waterbury where you can also tour the flavor graveyard to see some of the quirkier pints that are no longer with us.

When you’re ready to stretch your legs and give your stomach a break, the Shelbourne Museum is a must-see roadside attraction for art, history, and photography. Home to over 39 buildings, there’s everything from an old ship you can tour to a working carousel and vintage toys.

STOP: BURLINGTON

In the afternoon, it’s off to Burlington, which, if you’ve been to Boulder, may look familiar. Another quirky college town, Church Street is a virtual clone of pedestrian Pearl Street, and the city itself has been called “Boulder of the East” (although a bit more crunchy and counterculture-y than trustafarian) and right on the water.

Overnight in Vermont: Hotel Vermont (Splurge), Lang House on Main Street (Midrange), Mad River Barn (Budget)

Day 4: Connecticut

It’s our longest driving day, so get up early and begin the trek south because soon it’s back to the beaches. The Waterbury area to New Haven is a little over 3.5 hours, but you can break it up with stops en route. Hartford boasts the Mark Twain House and the beautiful Elizabeth Park Rose Garden, and further afield is Gillette Castle State Park and Sleeping Giant State Park.

Once in New Haven, make yourself a self-guided photo tour of Lighthouse Point Park and Carousel or pack a swimsuit and go for a dip on the beach. Wander East Rock Park and Pardee Rose Gardens, or charter a boat tour of Thimble Islands, a string of 25+ private islands which each have their own charm and appeal, many of which have one summer cottage per archipelago in case you’re looking for some prime real estate.

Overnight in New Haven: Graduate New Haven (Midrange), The Blake Hotel (Midrange), The Study at Yale (Midrange)

Day 5: Rhode Island 

Drive up the coast an hour and a half due east, and you’ll arrive in the ritzy town of Newport, Rhode Island, but not without a quick stop in Mystic, CT first. Mystic was one of Connecticut’s most popular seaports with a historic colonial downtown, steeped churches, and drawbridges. Stretch your legs and grab a bite.

Newport ended up being one of my favorite stops for its gorgeous landscaping and quaint waterfront. Wander the shops and restaurants around Bannister’s Wharf, tour the Breakers (the Vanderbilt summer home), follow the cliff walk, taking in the oceanside mega-mansions, or hop on a lobster boat and try your hand at fisherman life. If you’re up for one last thrill, the pedal-powered rail bikes are a great adrenaline rush to end the day. If you have more time, definitely tack on a day trip to Block Island or spend a weekend in Providence.

Overnight in Newport: The Cliffside Inn (Splurge), OceanCliff Hotel (Midrange), Wayfinder Newport (Midrange)

Day 6 – Optional Add-on: Boston & Cape Cod

From here, you can either fly home from Providence or Boston or continue on to Cape Cod. If you’re up for exploring the Cape, a handful of quaint beach towns await. Explore downtown Hyannis, play Goldilocks with the beaches (you have both saltwater and freshwater to choose from), eat your weight in lobster rolls from the roadside chowder shacks (or try a traditional Clam Bake!), and slowly make your way to Provincetown at the very tip.

One of the most LGBTQ+ friendly cities in the country, P-town is a maze of people watching, whale watching, and rainbow everything. It’s sensory overload in the best way possible.

Overnight in Cape Cod: The Wauwinet (Splurge), Frederick William House (Midrange), The Earl of Sandwich Motel (Budget)

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