A 2026 7-Day Itinerary From Someone Who Actually Lived There
Updated April 2026
I’ll be honest with you: I did not move to Maine planning to fall this hard. We parked Betty (our RV) near Bar Harbor in 2025 so my partner Brian could work as a registered Maine kayak guide for the season, and what was supposed to be six months of “let’s see how this goes” turned into me crying at my own Google Maps every time we crossed back over the Penobscot Narrows Bridge.
Six months of living on the coast. Six months of sunrise lobster boats, fog so thick you could lose a husky in it, Loki refusing to walk past a single tide pool, Freya pretending she’s never seen water before, and Caly (our supermutt) acting like every pebble beach is a personal gift.
So this isn’t a “I drove through Maine once and now I’m an expert” coastal Maine road trip itinerary. This is the road trip I’d hand my best friend if she texted me, “We’re flying into Boston, we have a week, GO.” Real stops, real food, real “wish I’d known this” notes, and yes, dog-friendly the whole way, because anything else feels like a betrayal of the Husky Industrial Complex that runs this household.
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How to Use This Coastal Maine Road Trip Itinerary
I’ve written this as a 7-day coastal Maine road trip from Boston Logan up to Acadia National Park, hugging Route 1 the whole way. You can absolutely:
Stretch it to 10 days and add Boothbay Harbor, Stonington, and the Schoodic Peninsula
Compress it to 5 days by skipping Kennebunkport or Wiscasset
Run it backward in the fall if you want to chase foliage from north to south
This is a road trip, not a death march. I built in space to actually sit with a coffee at the harbor for an hour without feeling guilty. We are anti-hustle in this house.
Pin it for later 📍
Quick-Reference: 7-Day Coastal Maine Road Trip Itinerary
Day 1: Boston → Kittery → Ogunquit → Kennebunkport (overnight)
Day 2: Kennebunkport → Cape Elizabeth → Portland (overnight)
Day 3: Portland exploration (overnight)
Day 4: Portland → Wiscasset → Rockland → Camden (overnight)
Day 5: Camden → Bar Harbor / Acadia (overnight)
Day 6: Acadia National Park (overnight)
Day 7: Acadia National Park → home (or optional Nova Scotia ferry add-on)
When to Take a Coastal Maine Road Trip
I have lived through every season on this coast, and I’ll tell it to you straight:
Late June through August – Peak season. Long days, warm-ish water (by Maine standards, which means your soul will leave your body for 90 seconds), every business open. Also, every business is crowded, accommodations book out months ahead, and Acadia parking is a personal vendetta.
September – My answer if you ask “when should I go?” The crowds thin, the water is technically warmer than July (counterintuitive but true), and most restaurants are still open.
First two weeks of October – Foliage. Just…foliage. Acadia in peak color is one of the most beautiful things on Earth, and I will die on this hill.
May & late October – Shoulder seasons. Cheaper, quieter, but plenty of seasonal restaurants and tours haven’t opened or have already closed. Read my Coastal Maine Packing List before you go because the weather will absolutely betray you.
November–April – Beautiful and very, very quiet. Bring real winter gear and lower your expectations for lobster shacks being open.
Before You Go: The Three Things You Cannot Forget
Six months of living here have burned three things into my brain that you absolutely need before you cross into Maine:
1. A real waterproof rain jacket. Maine rain isn’t romantic spitting rain – it’s full-commit drizzle that lasts six hours and can hit you on a “partly sunny” forecast. A $14 packable poncho will leave you soaked. You need a real waterproof, breathable shell.
2. Hiking shoes with grippy lugs. Acadia’s granite is unforgiving, and the trails are wet half the year. People hike the Beehive in flip-flops and require search-and-rescue. Don’t be that person.
For the full breakdown, every category, every season, check out my Coastal Maine Packing List (coming soon).
Need A Free Packing Checklist For Coastal Maine?
How to Get to Coastal Maine
Sure, you could fly into Portland International Jetport (PWM) and start there. And honestly, if you only have 4 or 5 days, do that.
But if you have a full week? Fly into Boston Logan International Airport (BOS). Flights are cheaper, rental cars are dramatically cheaper (Maine airport rentals in summer are a war crime), and the drive up Route 1 from the New Hampshire border into Maine is half the point of a coastal Maine road trip.
Rental car tip: Get something with decent gas mileage and a real trunk. You will buy more wild blueberry jam than you think.
Image alt: “Welcome to Maine, The Way Life Should Be” sign on Route 1 at the Maine state border.
…and now your Coastal Maine road trip begin!
The Ultimate Coastal Maine Roadtrip
Stop 1: Kittery, Maine – Your First Lobster Roll
Drive from Boston: ~1 hr 15 min, 65 miles
The second you cross into Maine, your job is to eat a lobster roll. I don’t make the rules.
My very first lobster roll, ever, was at Bob’s Clam Hut in Kittery – a Route 1 institution since 1956. Is it the best lobster roll in Maine? No. (That ranking lives in my 12 best lobster rolls in Maine post.) But there’s something sacred about your first one, and Bob’s nails the experience: paper basket, picnic table, slightly judgmental seagull staring you down.
What to order at Bob’s: Lobster roll with hot butter (or mayo – pick a side, this is a sport), a cup of clam chowder, and yes, lobster stew, even in July.
Right next door: The Kittery Trading Post, a Maine outdoor-gear icon. If you forgot rain gear, hiking shoes, or a fleece (and you did, see my Coastal Maine Packing List), this is your fix.
Dog-friendly note: Bob’s has outdoor picnic seating where well-behaved leashed pups are welcome. The pups have logged hours under that table.
Quick detour: Nubble Lighthouse, York
About 15 minutes off Route 1, Nubble Lighthouse (Cape Neddick) is the lighthouse you’ve already seen on a thousand calendars. You can’t walk to it; it sits on its own rocky islet, but the viewing area is free, the parking is generous, and it photographs beautifully in basically any weather.
Stop 2: Ogunquit – Beaches and the Marginal Way
Drive from Kittery: ~20 min, 10 miles
Ogunquit means “beautiful place by the sea” in Abenaki, and I have nothing snarky to add to that because they were not wrong.
Park near the village and walk Marginal Way, a 1.25-mile paved cliff walk that connects downtown Ogunquit to Perkins Cove. Leashed dogs are welcome before 10 AM and after 5 PM in summer (this is enforced; I learned the hard way that 10:02 is not 9:58). In the off-season, dogs are welcome anytime.
Where to eat: Bread & Roses Bakery (cinnamon morning buns, end of discussion) and Lobster Shack at Perkins Cove for, you know, the obvious.
If it’s swimsuit weather, Footbridge Beach is less crowded than the main Ogunquit Beach and has easier parking.
Stop 3: Kennebunkport – Cute Little Town, Big Lobster Energy
Drive from Ogunquit: ~25 min, 12 miles
Kennebunkport is the postcard. Walker’s Point (the Bush family compound), boutique-lined Dock Square, sailboats, and lobster boats heading out at dawn.
Where to eat in Kennebunkport
The Clam Shack (Kennebunk side of the bridge) – Their lobster roll has been crowned by Food & Wine, and it has earned that crown. Get the warm butter version.
The Ramp at Pier 77 (Cape Porpoise) – Casual, harbor views, “Pier 77 Style” lobster roll. Loki almost ate a man’s bait bucket here. Ask me about it.
Where to shop in Kennebunkport
Daytrip Society – curated, design-forward — makes me wish I had a bigger RV.
Beach Grass – Beach-house decor I cannot have because I live in 240 square feet.
Goose Rocks Beach allows leashed dogs before 9 AM and after 5 PM in summer. Plan accordingly. The huskies don’t care about your sleep schedule, and neither does the parking lot.
Stop 4: Cape Elizabeth – Two Lighthouses, One Quick Stop
Drive from Kennebunkport: ~45 min, 34 miles
Pull off Route 1 for Two Lights State Park in Cape Elizabeth. Twin lighthouses, dramatic rocky coast, a great leg-stretcher for both you and the pups. Dogs welcome on leash.
While you’re here, eat at The Lobster Shack at Two Lights – open seasonally (May–October). Order at the window, eat on a picnic table, watch the surf hammer the rocks, ignore the seagulls (or don’t, your sandwich, your choice).
Five minutes down the road is Portland Head Light at Fort Williams Park – the most-photographed lighthouse in America for a reason. The park itself is 90 acres of dog-friendly green space with ocean views.
The Well Worn Shoes Insider Tip: If you didn’t stop at the Lobster Shack at Two Lights, check out the Bite Into Maine food truck at Fort Williams Park. Seriously, one of my favorite lobster rolls in Maine!
Stop 5: Portland, Maine – The Best Small City in New England (Fight Me)
Drive from Cape Elizabeth: ~18 min, 8.5 miles
I love Portland. It’s gritty and stylish and unpretentious, and the food scene punches three weight classes above its size. If you only have one day here, I have a full breakdown in my One Day in Portland, Maine guide.
Where to eat in Portland
Bite Into Maine (food truck at Fort Williams or now in Scarborough) – Their Maine-Style and Connecticut-Style lobster rolls are next-level. Yes, get both. We’re on vacation.
Eventide Oyster Co. – Oysters with horseradish ice. Brown butter lobster bun. This is a religious experience.
Duck Fat – Belgian fries fried in duck fat with truffle ketchup. I’ve thought about these on my deathbed, and I am alive.
The Holy Donut – Maine-potato donuts. The dark chocolate sea salt is the move.
Standard Baking Co. – Best morning bun in the state. I will defend this position in court.
What to do in Portland
Walk the Eastern Promenade – paved trail along Casco Bay, beautiful at sunset, dog-friendly.
Old Port cobblestone streets – bring real shoes, those cobbles are a personal injury lawsuit waiting.
Portland Observatory – historic signal tower with panoramic views.
Casco Bay Lines ferry – Cheapest ocean cruise in Maine, runs to Peaks Island and beyond.
Where to stay in Portland
The Press Hotel (boutique, in the old newspaper building, dog-friendly with a fee)
Inn at Diamond Cove (on Great Diamond Island, ferry-only, dreamy)
Stop 6: Wiscasset – “The Prettiest Village in Maine” (And the Famous Lobster Roll)
Drive from Portland: ~48 min, 45 miles
Wiscasset bills itself as the prettiest village in Maine, and there’s a strong case for it with riverfront, historic homes, and the legendary line outside Red’s Eats.
Red’s has been serving Maine’s most-debated lobster roll since 1938. Down East Magazine has crowned it #1 more times than I can count. Is it actually the best? Read my 12 Best Lobster Rolls in Maine and decide for yourself. I will tell you this: the line moves, and the lobster roll is a full lobster’s worth of meat piled on a buttered bun. It is a lot of lobster, in the best way.
If the line at Red’s is melting your brain, Sprague’s Lobster is across the street with comparable rolls and a quieter waterfront patio. Locals are split. Order one of each and be the deciding vote.
Stop 7: Rockland – Art, Lighthouses, and a Genuinely Cool Downtown
Drive from Wiscasset: ~43 min, 33 miles
Rockland is criminally underrated. It’s got an artsy, working-waterfront vibe with galleries, working lobster docks, schooners in the harbor, all without feeling precious about itself.
What to do in Rockland
Farnsworth Art Museum – Wyeth family work in particular. Worth a couple of hours.
Rockland Breakwater Lighthouse – A 0.9-mile granite jetty walk on top of the breakwater out to a cute little lighthouse. Dog-friendly, but mind the gaps in the granite slabs and skip it in heavy weather.
Rockland Harbor Trail – Easy paved walk with the pups along the working waterfront.
Where to eat in Rockland
McLoon’s Lobster Shack (technically South Thomaston, 10 min away) – gorgeous harbor views, get the lobster roll with half mayo, half warm butter (yes, it’s allowed), and a Gifford’s ice cream after. Expect a wait, but it’s gorgeous so just take in the views and enjoy the vibe!
Primo – If you want a special-occasion farm-to-table dinner, this is the one.
Rock City Cafe – Coffee and pastries before you hit the road.
Where to stay in Rockland
Glen Cove Inn (mid-range, dog-friendly)
250 Main (boutique, modern, harbor-front)
Stop 8: Camden – The Jewel of the Maine Coast
Drive from Rockland: ~16 min, 8.3 miles
If Camden doesn’t make you fantasize about chucking your career and running a B&B, I don’t know what will. Mountains literally rise out of the harbor here; it’s a rare place on the East Coast where you can hike a peak and look down at a working schooner port.
Hike Mount Battie in Camden Hills State Park (1.0 mile up, steep but short, panoramic Penobscot Bay views, dogs welcome on leash) – or drive the auto road if you don’t feel like a stair-master moment.
Camden Harbor Park & Amphitheater – Picnic lunch, watch the schooners.
Schooner Day Sail – Camden is one of the windjammer capitals of the world. Surprise Sailing Charters and Schooner Olad both do shorter day sails.
Curtis Island Lighthouse – view from the Curtis Island Overlook on Bay View Street.
Mount Megunticook – the highest mainland mountain on the Atlantic Coast. Bigger climb, bigger payoff.
Marriner’s Restaurant – old-school New England diner, blueberry pancakes, easy on the wallet.
Long Grain – Thai-leaning, tiny, you’ll need a reservation, worth it.
Sea Dog Brewing – patio overlooking the falls; pups welcome on the patio.
Where to stay in Camden
Whitehall Inn (historic, sprawling porches, walkable to downtown)
Lord Camden Inn (boutique, in the heart of the village)
Camden Hills State Park Campground (tent or RV, May–October, dog-friendly)
Stop 9 (The Big One): Bar Harbor & Acadia National Park
Drive from Camden: ~1 hr 30 min, 80 miles
Okay. Deep breath. This is where I lived for six months, and I could write you a 12-part novella about it. Let me restrain myself to the highlights, with links to the deep dives.
Why Acadia is special
Acadia is 47,000 acres of granite mountains running directly into the Atlantic. It’s where the mountains touch the sea. It’s the only place in the United States where you can stand on the highest point on the Eastern Seaboard (Cadillac Mountain) at sunrise and be the first person in the country to see the sun (October 7 to March 6, fun fact for your group chat).
It’s also one of the most dog-friendly national parks in the U.S., and that mattered enormously to us. More on that below.
Things you absolutely cannot skip
Sunrise on Cadillac Mountain (timed-entry vehicle reservation required May–October – book it on Recreation.gov the second the window opens). But don’t worry if you don’t get Cadillac Mountain reservations, I promise, it’s not the end of the world, and there are plenty of beautiful places to take in a sunrise. Full breakdown in my Best Sunrise Spots at Acadia guide.
Park Loop Road (27 miles, hits Sand Beach, Thunder Hole, Otter Cliff, Jordan Pond)
Jordan Pond House popovers (with strawberry jam, dog-friendly outdoor seating)
Ocean Path from Sand Beach to Otter Cliff (2 miles, mostly flat, dog-friendly, jaw-dropping)
Bass Harbor Head Light at sunset (the iconic shot, on the quiet side of the island)
I’ve done the South Ridge, and even in the middle of summer, it can be COLD up there, even in July (think 40s and windy). In October, it’s near freezing. You will need a beanie, a puffy, and ideally hand warmers, regardless of the season. I have personally witnessed someone in shorts cry at the summit.
Acadia allows leashed dogs (6 ft max) on 100+ miles of trails and all 45 miles of carriage roads. After six months of walking these with Loki, Freya, and Caly, my MVP picks:
Trails dogs are NOT allowed on: Precipice, Beehive, Ladder Trail to Dorr Mountain, Beech Cliffs, Perpendicular, Jordan Cliffs. These have iron rungs and ladders. Just don’t.
Acadia’s granite trails are rough on paw pads, and the 6-foot leash rule is non-negotiable (no flexi-leashes, rangers will absolutely call you on it). Here’s what we never hit the trail without:
Coffee Hound at The Stadium (62 Main) – Nitro Chai, popovers with blueberry jam. Veteran-founded, woman-owned, take-out only.
Acadia Perk (5 Firefly Lane) – Blueberry Macchiato, Blueberry Matcha Latte. Across from the Village Green.
Jeannie’s Great Maine Breakfast (now at 8 Cottage Street, moved for the 2025 season) – Wild Maine blueberry pancakes.
Jordan’s Restaurant – Opens at 5 AM for pre-Cadillac sunrise hikers. Wild Maine blueberry pancakes with a $2 upcharge for wild blueberry syrup that is worth your last dollar.
CJ’s Big Dipper – Old-school ice cream, red-and-white striped awning, eat it on a bench.
West Street Cafe – Everything I’ve ever tried here is so good!
Side Street Cafe – Lobster mac & cheese, year-round, dog-friendly patio.
Where to shop in Bar Harbor
Sherman’s (the oldest bookstore in coastal Maine, est. 1886),
Bark Harbor (everything for the dogs — Loki and Freya know this address),
Sailor and Hook (vintage nautical), In The Woods (responsibly-sourced wooden goods),
Camping (dog-friendly): Blackwoods Campground (most central), Seawall (quiet side, mosquito warning in June), Schoodic Woods (off-island, blissfully quiet). Full breakdown: Camping at Acadia.
Glamping: Under Canvas Acadia
Inns: Ullikana Inn, Ivy Manor Inn (mid-range), Bar Harbor Inn (waterfront, splurge)
RV travelers: We’ve stayed at several parks here – search for sites with full hookups and book by January for summer.
Need a Must-Do Checklist?
Optional Add-On: The CAT Ferry to Nova Scotia
If you have a couple of extra days, the CAT Ferry from Bar Harbor to Yarmouth, Nova Scotia, is a 3.5-hour high-speed crossing, currently around $105 per adult one-way. From Yarmouth, you can road-trip up to Halifax or all the way to Cape Breton Highlands National Park (one of my favorite parks anywhere, write that down).
You can take cars, RVs, motorcycles, bikes, or walk on as a foot passenger. Bring your passport and check current schedules; the route runs seasonally.
Road Trip Driving Essentials (Don’t Skip This)
Coastal Maine driving has some genuine quirks: long stretches between towns, patchy cell service (especially on Schoodic and stretches of Route 1 north of Camden), and at least one moment where your GPS will give up entirely. Here’s what’s earned permanent residence in our truck after six months:
How many days do you need for a coastal Maine road trip? Seven days is the sweet spot — enough to drive Route 1 from Kittery to Acadia without rushing, with two full days at Acadia National Park. Five days works if you skip the southern coast and start in Portland. Ten days gives you breathing room to add Boothbay Harbor, Stonington, and the Schoodic Peninsula.
What’s the best time of year for a coastal Maine road trip? September is my top pick — warm-enough water, all the seasonal businesses still open, and noticeably fewer crowds than July or August. Early October is a close second for fall foliage in Acadia. Avoid late November through April unless you genuinely love quiet, cold, and closed lobster shacks (some of us do).
Should I fly into Boston or Portland for a coastal Maine road trip? Fly into Boston Logan (BOS) if you have 7+ days – flights and rental cars are significantly cheaper, and you’ll enjoy the southern coast (Kittery, Ogunquit, Kennebunkport). Fly into Portland (PWM) if you only have 4–5 days and want to skip ahead.
Is a coastal Maine road trip dog-friendly? Yes, exceptionally so. Acadia National Park is one of the most dog-friendly national parks in the U.S., and Maine’s coastal towns (Bar Harbor, Camden, Rockland, Kennebunkport) all have multiple dog-friendly restaurants, beaches, and trails. Just check seasonal beach restrictions, which usually limit dogs to early mornings and evenings, May through September.
How long does it take to drive coastal Maine from Kittery to Bar Harbor? Without stopping, the drive from Kittery (the Maine/NH border) to Bar Harbor is about 5 hours and 45 minutes, covering ~280 miles, mostly on I-95 and Route 1. With stops, it’s a 5–7 day road trip, and the stops are the entire point.
What is the most scenic stretch of the Maine coast? Hot take from someone who lived there: the stretch from Camden through Bucksport to Bar Harbor, especially crossing the Penobscot Narrows Bridge, is the most dramatic. For sheer rocky-coast iconography, you can’t beat Acadia’s Park Loop Road between Sand Beach and Otter Cliff.
Do I need a rental car for a coastal Maine road trip? Yes. Public transit between coastal Maine towns is essentially nonexistent. Inside Acadia National Park, the free seasonal Island Explorer Shuttle is excellent for cutting traffic, but you still need a car to get there.
Are there reservations required for Acadia National Park? A timed-entry vehicle reservation is required for Cadillac Mountain Summit Road during peak season (typically late May through late October). You’ll also need a standard park entrance pass (or America the Beautiful pass) year-round. Book Cadillac reservations on Recreation.gov as soon as the window opens — they go quickly.
A Final Note From Someone Who Didn’t Want to Leave
Six months in this place, and I still left a piece of my heart somewhere on Otter Cliff. Brian guided kayak trips through the islands all summer; Loki perfected the art of falling asleep on a pebble beach; Freya made it her mission to greet every tourist on Main Street; and Caly lived her best mutt life, chasing salt air.
Coastal Maine has the rare quality of being beautiful enough to live up to the photos and lived-in enough to feel real. Go. Take your time. Eat the lobster roll. Bring the dog. Stay an extra day.
If you have questions before you go, drop them in the comments. I read every one.
Those photos make me wish I could visit there soon! Especially Maine.
Hi Melanie!
Thank you so much! Maine is absolutely gorgeous and I can’t wait to go back.
I’ve heard how beautiful Maine is but I’ve never had a chance to visit the state. Thank you for compiling this great list to make planning easy 🙂
Hi Shelia!
You’re so welcome! Maine is absolutely stunning!