A great New England road trip: enjoy your vacation in Maine 

The cherry of the American northeast on the tippy-top of the New England region is the sweet state of Maine, home of butter-soaked seafood, easy-going adventures and culture-packed beach towns. With so much coastline to cover, a road trip is inevitably everyone’s top choice, allowing for easy, scenic drives between the state’s much-loved nature reserves and its cool coastal villages. Discover the history of Maine along the journey, stopping at hidden settlements for a taste of the state’s strong nautical history and, of course, it’s cardinal catch of the day. We’ve compiled a selection of the best coastal towns in Maine and travel tips so you don’t have to.

Tailor Made Journey

Let Us Plan
Your Perfect Vacation

Mr Hudson designs unique and luxurious vacations for sophisticated travelers who prioritize beauty and style.

Book Your Luxury Vacation With Mr Hudson Book Your Luxury Vacation With Mr Hudson Book Your Luxury Vacation With Mr Hudson

Photo: Ante Hamersmit

FYI on the State of Maine

Peruse a map of Maine and you’ll soon see that the state’s craggy coastline is the prime path for a road trip. Route 1 (AKA US-1 North) will take you past a plethora of harbours and cutesy fishing villages, with the choice of where to stop all down to you. Regardless of where you choose to stay, you’re likely to see gay-friendly attitudes across the state, with the strongest gay community located in the city of Ogunquit.

Best time to visit Maine

Visiting Maine in any season has its merits, but some months come off worse than others. Summer in Maine runs from June through to September, with average temperatures in July and August around 21° Celsius, the perfect weather for beach days and coastal drives.

Maine in the fall is not to be sniffed at either, as this is when foliage across New England erupts into shades of red, yellow and orange. Maine fall colours are best captured from September to early November when views from within the state parks and atop the mountains are most spectacular. Visit Maine in the fall or winter months and you’ll also avoid the busiest tourist times, making it easier to get a table at any of Portland’s buzzing restaurants.

Photo: Mark Tegethoff

Photo: Benjamin Francois

US road trip itinerary – Maine

Maine is the largest state in New England, bordered by Canada in the north and the Atlantic Ocean in the east and south, with a coastline stretching all the way from warmer coastal settlements to the chillier Great North Woods. While navigating the coastline, adventurers have to opportunity to try their hand at kayaking, whale watching, camping and more. Let’s break the journey down into 10 days…

Day 1 & 2: Ogunquit

For this trip we follow our compasses and head from south to north, ending at the Canadian border. We start in gay Ogunquit, a small city just 66 miles north of Boston and home to Maine’s strongest gay community, rivalled only by nearby Portland. Not to be missed regardless of your orientation, Ogunquit is a small fishing village turned artists’ haven featuring three miles of sandy beaches along with dance clubs, B&Bs and busy restaurants which sit alongside galleries and art museums.

Spanning just four square miles, Ogunquit is one of the most walkable cities in the US, split between two key areas known as the Village, where the gay bars lie, and Perkins Cove, where a quaint New England vibe permeates the residing restaurants and shops. For Atlantic Ocean realness, head along the cliff path at Marginal Way for fantastic views and snack opportunities between Perkins Cove and Shore Road. If walking is not your gig, then hitch a ride on the circular town trolley, pausing a while on the grassy dunes of Ogunquit Beach to look out over the Atlantic Ocean in the east and Ogunquit River in the west. There are arguably more things to do in Ogunquit Maine during the summer, with musicals staged at the Ogunquit Playhouse’s summer theatre and beach sculpture exhibitions.

Ogunquit | Photo: Justin Bisson Beck

Where to stay in Ogunquit: Of the top Ogunquit Maine hotels, we highlight Nellie Littlefield Inn & Spa an adults-only B&B blending elegant period décor with contemporary stylings in northern Ogunquit; Puffin Inn is a former sea captain’s home featuring flower gardens just minutes from the beach, and The Trellis House is a gay-owned property boasting ocean views and English garden elegance in southern Ogunquit.

Day 3: Kennebunkport & Old Orchard Beach

Once we tire of Ogunquit, we drive just 21 minutes (along the US-1 North and State Route East) to Kennebunkport. While you might be itching to get on the road, you won’t regret spending the morning in this 18th-century town, taking in the idyllic harbourside, Goose Rocks Beach and local craft stores dotted along the front. Cross the beach to the tiny fishing village of Cape Porpoise or explore the hiking trails within the Rachel Carson National Wildlife Refuge, all before diving into Dock Square’s exciting foodie scene which centres on fresh local seafood, with specialities such as fried clams and buttered lobster.

Opt to spend longer here, booking a night at a shore-side mansion or a cutesy B&B, or with the sun high in the sky, drive on to Old Orchard Beach, a more happening area just 30 minutes from Kennebunkport, popular for its wide sandy beach and carnivalesque atmosphere. Busy yourself with a walk up The Pier, indulging in shopping, dining or clubbing after sundown. Of all the things to do in Old Orchard Beach, the young at heart might head to Palace Playground for amusement park rides and carnival games. In the summertime, however, the action is delivered directly to the beach, with music festivals, fireworks and even a hot air balloon festival set up on the sand.

Photo: D. Snake

Photo: Tyler Nix

Mr. Hudson highlight image

Portland offers up a metropolitan art scene, myriad museums and award-winning dining opportunities, all within the beautifully preserved setting of the 17th-century Old Port and downtown areas

Day 4: Cape Elizabeth 

There’s no hurry to wake on day four as our next destination takes us just 28 minutes along the US-1 North to Cape Elizabeth, a tranquil town just outside of Portland. Choose between adventures into Crescent Beach State Park for forest trails that wind towards sandy beaches, or enjoy a rocky climb to the Cape Elizabeth lighthouse followed by an ocean-side picnic at the Two Lights State Park. Wannabe hunter-gatherers might also consider charting a fishing boat in nearby Saco or Scarborough.

Day 5 & 6: Portland

Another short drive along ME-77 North leads us to Portland, Maine’s largest city with a humble population of 66,700. Small yet vibrant, Portland has all the Maine staples, including a bustling harbour and all manner of finger-licking seafood. More than that, however, Portland offers up a metropolitan art scene, myriad museums and award-winning dining opportunities, all within the beautifully preserved setting of the 17th-century Old Port and downtown areas.

Venture off-road to discover Portland’s secret beaches, where old lighthouses stand atop coastal bluffs and lobster rolls come at you from all angles. Although not quite on the same level as big-hitters like San Francisco and Denver, Portland has its own unique charm with friendliness and authenticity not found elsewhere. Portland’s petite size might mean that it lacks both sex clubs and college nights, but the city more than makes up for this with its melting-pot of mixed bars, clubs and restaurants. If scouting for boys is on the agenda, make a pitstop at Boothbay Harbor where gay men come to mingle.

Photo: Nicola Giordano

Day 7: Damariscotta-Newcastle

Day seven takes us to the twin villages of Damariscotta-Newcastle, with a journey time of just one hour from Portland along the I-295 North and US-1 North. Considered a must-stop destination, these two towns flank the Damariscotta River, joined in the middle by the pedestrian-friendly Main Street Bridge. Stroll through downtown to discover the village’s independent boutiques and eateries before expanding your view and heading out on winding backroads towards neighbouring villages such as Round Pond and New Harbor, ending the day with a sunset beside the Pemaquid Point Lighthouse. Oyster lovers should note that Damariscotta is known as the ‘Oyster Capital of New England’, holding not one but two oyster festivals each year!

Day 8 & 9: Camden

When the aphrodisiac effects of yesterday’s shellfish wear off, we hit the road once more and head to Camden (37 minutes via the ME-90 East and US-1 North). One of the most popular coastal day trips in New England, Camden lies nestled within West Penobscot Bay boasting an impressive art scene within an 18th-century village setting all amidst spectacular parks and natural scenery. If the schedule for the opera house or annual Shakespeare Festival doesn’t suit, get out of town to discover gorgeous bay views from Camden Hills State Park or take to the water for various excursions including windjammer sailing tours, sea kayaking, fishing charters or a cheap and cheerful ferry to the nearby islands. For more info on things to do in Camden Maine, head to the VisitMaine website.

Bar Harbor | Photo: David Mark

Mr. Hudson highlight image

Way out in the Gulf of Maine and far from the main tourist trail, Stonington is an authentic harbour town, while Deer Isle – the gateway to Stonington – offers winding coastal roads and dramatic 360° scenery

Day 10 & 11: Castine & Stoningtop - Deer Isle

One hour on from Camden lies the historic town of Castine (accessible via US-1 North and the ME-166) on a small outcrop lapped by both the Bagaduce River and Penobscot Bay. Once the capital of Acadia, Castine seduces visitors with its faded beauty and huge mansions once fought over by the French, Dutch and English. While the town centre is full of quaint eateries, shops and B&Bs, across town the viewpoint at Dyce Head is not to be missed, nor the untouched nature at Wadsworth Cover Beach and Witherle Woods.

More unspoiled coastline is yours for lounging on at Stonington, just 40 minutes from Castine via ME-15 South. Way out in the Gulf of Maine and far from the main tourist trail, Stonington is an authentic harbour town, while Deer Isle Maine – the gateway to Stonington – offers winding coastal roads and dramatic 360° scenery. Deer Isle is also famed among sculptors and architects for its granite, while Stonington is a lobster town through and through.

Photo: Mael Balland

Photo: Aaron Weiss

Day 12 & 13: Bar Harbor  & Acadia National Park

Next we venture to Bar Harbor (1 hour and 15 minutes via ME-15 North, ME-172 North and ME-3 East) where we’ll rest up, hemmed in on either side by the epic Acadia National Park and the rugged straits of Mt. Desert Narrows. Popular among artists and outdoorsy types, Bar Harbor provides the perfect jumping-off point for Acadia National Park hiking trails but also holds buckets of Downeast charm in its own right. Get a feel for the island with a boat tour excursion (whale watching is also available!), or simply tour the town by tram or on foot, discovering local art and handicrafts on Main Street. Stroll along Shore Path for a glimpse at the town’s luxury yachts and sea parks and, when the time comes, dine on a variety of local produce, including the freshest local seafood.

With your base set in Bar Harbor, we awake the next day for our first foray into Acadia National Park. Simply breathtaking from all angles, Acadia offers up the region’s best scenery amidst acres of dense forest. Spanning rocky coastline and mountain peaks, Acadia is fully accessible by car, thanks to the 27-mile Park Loop Road. Stop off at various points, tackling the granite cliffs on Precipice Trail or appreciating the Atlantic views from Schoodic Point. Come to Acadia in October for the best look at Maine in the fall, or, whatever the season, enjoy wildlife watching, rock climbing, hiking, kayaking, biking and more. In Acadia National Park camping is also a top choice, allowing for an authentic retreat into nature.

Acadia National Park | Photo: Mick Haupt

Day 14: Lubec

Our final stop brings us to the northeast coastline beside the Canadian border, where a more rustic experience awaits. Less built-up than previous towns, Lubec is Maine at its wildest. A working town, Lubec is most alive at the dock where lobster tugboats moor and humble eateries serve up the freshest catch. If time allows, do a nature trail towards the rocks at Quoddy Head Lighthouse where you’ll catch a superb view of the Bay of Fundy and a possible encounter with Atlantic Puffins.

Want to simplify luxury travel planning?

Whether you want a resort vacation, wildlife safari, city break, luxury cruise, wellness retreat, honeymoon, once-in-a-lifetime adventure or weekend escape, the trip curation experts at Mr Hudson make travel planning a breeze. Find out how we can handle the finer details of vacationing in style.

Photo: Donald Giannatti

Subscribe to our newsletter

You can unsubscribe at any time by clicking the link in the footer of our emails. We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing.

Sign up for exclusive insider promotions