3 Day Boston To Maine Road Trip – Kennebunkport, Portland & Bar Harbor Itinerary
Planning a 3 day Boston to Maine road trip? Whether you’re craving coastal charm, world-class seafood, or a quick dose of nature, this long weekend getaway packs in New England’s greatest hits (including Kennebunkport, Portland and Bar Harbor!)
You’ll walk cobblestone streets, watch the sunset from a lighthouse, and finish off every day with lobster rolls and local beer. The best part? It’s all totally doable in just three days, so pack your backs for a long weekend getaway from Boston!
In This Article:
- Full 3 day itinerary from Boston to Bar Harbor Maine
- What to see and do from Boston to Portland, Kennebunkport, and Acadia
- Where to eat, stay, and stop along the way
- Suggested itinerary extensions if you have more time
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Boston To Maine Road Trip
This 3 day road trip from Boston to Bar Harbor Maine is a great way to explore New England! In total, it’s 5 hours to Bar Harbor from Boston so you’ll have about 10 hours of drive time with this itinerary.
If you’d prefer to spend less time driving you can skip Bar Harbor and shorten the trip by taking a road trip from Boston to Portland Maine instead. This is less than 5 hours of driving.
Boston To Maine Road Trip Map
This map will help you plan your Boston to Maine road trip! I’ve pinned all the best stops and labeled them with icons to note the type of activity they are.
How To Use This Map:
1. To open in a new tab, click [] in the top right corner of the map.
2. To save to your Google Maps account, click ☆ (you must be signed in to Google).
3. To use during your trip, open Google Maps on your phone, select “You” from the bottom bar, scroll down and click the maps icon for a list of your saved custom maps.
Day 1: Drive From Boston to Portland Maine
Start your day bright and early in Boston, especially if you’re heading out on a weekend. Traffic can get heavy by late morning, so aim to be on the road early! It’ll potentially save you hours on the road in traffic.
Before you go, consider grabbing breakfast at Flour Bakery (my favorite! I used to stop here on my way to work when I lived in Boston) or Tatte, another local hot spot.
TIP: If you need a rental car for your trip, I recommend DiscoverCars.com. When I lived in Boston, it was cheaper to rent a car when I needed one, rather than pay to park/maintain/insure my own. DiscoverCars.com has a huge inventory and negotiates the best rental car prices. They also allow free cancelation up to 48 hours before your pick-up time.
Morning: Hit the Road from Boston to Kennebunkport Maine
It’s just 90 minutes from Boston to Kennebunkport for your first official taste of Maine. This postcard-perfect town is filled with boutiques, lobster shacks, and stunning ocean views. Park near Dock Square and wander the waterfront shops.
Can’t Miss Things To Do In Kennebunkport, Maine:
- Drive along Ocean Avenue towards Walker’s Point overlook to see St. Ann’s Episcopal Church and some gorgeous beach homes (including the Bush family compound)
- Grab a lobster roll at The Clam Shack (yes, it lives up to the hype)
- Browse independent bookstores and antique shops downtown
If you’re visiting in summer, consider a quick paddleboard or kayak rental for an hour on the water, or take a short scenic drive to Goose Rocks Beach to stretch your legs.
Afternoon + Evening: Arrive in Portland from Boston
Portland is a small city with big flavor, about 30 minutes past Kennebunkport and a total of 2 hours from Boston to Portland Maine.
After checking into your hotel or Portland vacation rental, head to the Old Port District. The cobblestone streets are lined with local boutiques, craft breweries, and some of the best food in the Northeast.
Top things to do in Portland, Maine:
- Visit Portland Head Light in Cape Elizabeth (sunset is perfect here)
- Take a sunset harbor cruise or go on a whale watching tour (book ahead!)
- Sample craft brews at Bissell Brothers or Allagash Brewing
- Check out local art galleries or the Portland Museum of Art
- Ride the Maine Narrow Gauge Railroad for scenic waterfront views
- Grab a gelato at Gorgeous Gelato or a craft cocktail at Blyth & Burrows
Dinner Picks:
- Eventide Oyster Co: order the brown butter lobster roll
- Central Provisions: tapas-style with killer cocktails
- Via Vecchia: Italian in a stunning setting
- Fore Street: wood-fired fare and regional ingredients
- Duckfat: elevated comfort food
Where to Stay In Portland, Maine:
- The Press Hotel: a historic, stylish, centrally located option
- Vacation rental in the Old Port: for walkability
- Blind Tiger Guest House: a boutique B&B experience
- The Francis: a renovated mansion with spa options
Day 2: Explore Portland + Drive to Bar Harbor
Fuel up for your next stretch with another delicious morning in Portland (I definitely recommend trying The Holy Donut!). Whether you’re starting slow or eager to check off a few more sights, this city rewards early risers with calm streets, great eats, and salty sea air.
Morning: Chill Portland Vibes
Start your morning with a coffee from Tandem or pastries from Standard Baking Co. If you didn’t get to Portland Head Light yesterday, now’s your chance for a quick visit.
If you’re up for more things to do in Portland, Maine, hit up:
- Eastern Promenade for waterfront views
- Shops on Exchange Street
- Browse indie bookstores like Print: A Bookstore
- Stop at The Holy Donut for potato-based donuts with a cult following
- Explore the Portland Observatory or go for a walk along Back Cove Trail
Complete The Drive From Boston to Bar Harbor (Approx. 3 hours From Portland)
Hop back on the road for the drive to Bar Harbor from Portland, which is about 3 hours. You can go straight up I-295 for an easy highway drive, or detour along Route 1 through coastal towns like Camden or Belfast for lunch and scenic charm (which will add about 30 minutes of drive time but is definitely worth it!)
Lunch ideas:
- Archer’s On The Pier: a Rockland favorite with seafood and waterfront views
- Camden Deli: fresh food, counter-service and a rooftop harbor view
- Rosalie’s Pizza: in Bar Harbor if you want to power through and eat when you arrive
Afternoon + Evening: Arrive in Bar Harbor
Settle into your hotel or inn, then hit the Bar Harbor Shore Path for a relaxing walk along the water. It’s the perfect way to stretch your legs before dinner.
Things to do in Bar Harbor before dinner:
- Walk along the sandbar to Bar Island during low tide
- Stop at Ben & Bill’s for lobster ice cream (yes, it’s a thing)
- Pop into small galleries and souvenir shops
- Watch the sailboats from Agamont Park
Dinner Options:
- Side Street Cafe: casual and delicious burgers and bar food
- Galyn’s: more upscale, seafood & ocean views
- Havana: a Caribbean twist on Maine ingredients like seafood paella
- The Reading Room: classic coastal dining with a live piano at Bar Harbor Inn
Where to Stay:
- Bar Harbor Grand Hotel – An elegant hotel modeled after a 19th-century mansion, with spacious rooms and a prime location.
- Acadia Inn – A family-friendly hotel with direct trail access to Acadia National Park.
- Little Fig Hotel (Formerly Quimby House) – A stylish, recently updated boutique hotel, walkable to downtown Bar Harbor.
Day 3: Acadia National Park + Return to Boston From Maine
On the final day of your Boston to Bar Harbor Maine road trip spend the morning exploring Acadia National Park before starting the 5 hour drive to Boston.
Morning: Explore Acadia National Park
Acadia is one of the most beautiful national parks in the U.S., and even if you only have a few hours, it’s 100% worth visiting. Start early to beat the crowds, especially if you’re visiting between July and September.
Top things to see in Acadia in a half day:
- Sunrise on Cadillac Mountain (reservations required May – October)
- Jordan Pond + popovers at Jordan Pond House
- Drive Park Loop Road: Sand Beach, Thunder Hole, Otter Cliffs
- Walk the Ocean Path for incredible coastal views
- Stop at Sieur de Monts for the Wild Gardens of Acadia
TIP: If you’re short on time, rent an e-bike and explore the Carriage Roads for a fun, low-effort way to see more of Acadia National Park.
If you have extra time, consider one of these quick hikes:
- Beehive Trail: short, but steep, 1.5 mile loop with stunning water views.
- Gorham Mountain Loop: 3 mile dog friendly hike in Acadia with ocean scenery
- Precipice Loop: 2.7 miles, but mostly straight up (1,000 ft gain) with multiple ladder sections.
READ MORE: Hiking gear for beginners (what you need, and what you don’t)
Lunch + Begin Drive Back to Boston
After your Acadia visit, grab lunch in Bar Harbor. I recommend Cafe This Way for the corned beef hash or Choco-Latte Cafe for a to go sandwich on one of their homemade bagels.
Optional Stop:
- Freeport: Grab dinner and visit the LL Bean flagship store
- Portland (again): Early dinner at Duckfat or Highroller Lobster Co.
- Newburyport: Historic charm and great rest stops just before hitting Boston
Additional Tips for Your Boston to Maine Road Trip
There are so many ways to customize the drive from Boston to Bar Harbor Maine. It’s a great weekend trip from Boston, but you can easily extend your road trip to a week or more!
I recommend heading from Boston to Bar Harbor Maine along the coastal route (Rt-1), and then returning on Rt-295 to save some time.
These are some additional things to consider when planning your Boston to Maine road trip…
Best Time to Go
Late spring through early fall is ideal for visiting Maine from Boston. If you’re visiting in October, you’ll catch stunning autumn colors on your New England fall road trip. Just remember to book hotels early because July through October is peak season.
TIP: June and September tend to offer the best mix of pleasant weather and fewer crowds.
🌱 Spring: Fewer crowds, blooming flowers, cool temps
🌻 Summer: Peak travel season, long daylight, all activities open, best season for whale watching
🍁 Fall: Crisp air, brilliant foliage, busier but stunning. Fall in Acadia National Park is magical.
❄️ Winter: Many attractions close or reduce hours; best avoided for this Boston to Maine road trip itinerary unless you’re specifically visiting for winter activities
Tips For Driving From Boston To Maine
- Avoid rush hour leaving Boston and returning on Sunday. (There’s a reason they call MA drivers Mass-holes!)
- Consider a small SUV or compact rental car for easy parking in small towns
- Keep cash or a credit card handy for parking meters, park fees and spontaneous stops at roadside stands with local produce and homemade goodies
- Stop at local visitor centers for maps, tide charts, and helpful advice from locals
What to Pack For A Road Trip From Boston To Maine
- Layers: coastal Maine weather can change fast
- Rain jacket
- Hiking shoes or comfy sneakers for exploring Acadia
- Binoculars for whale watching or bird spotting in Acadia National Park
- A daypack for short hikes or walks
- Power bank for your phone, especially when using maps
- Reusable water bottle and snacks for hiking days
- Sunscreen, sunglasses, and bug spray (definitely don’t forget the bug spray!)
Booking Ahead
Bar Harbor, especially during peak season (July – October), fills up quickly. Late reservations may be possible, but you’ll pay more for them.
The Maine coast has fewer big box hotels, and more charming (but small) boutique hotels, so reservations can be harder to snag during the summer and fall.
Acadia National Park only offers camping options, and those fill up months in advance. Additionally, Cadillac Mountain requires a reservation during the summer months so snag those ahead too! (some are released 90 days in advance, the rest 2 days in advance)
Cell Service
Cell reception can be spotty at best in Acadia National Park and parts of coastal Route 1 between Boston and Maine. Download offline Google Maps and consider saving lodging or ticket confirmations as screenshots so you can access them without cell connection.
Gas & Restrooms
Restroom stops can be sparse in rural areas on the drive from Boston to Maine. Plan your gas stops in towns like Ellsworth, Freeport, or Wiscasset, where there are also clean, public facilities.
TIP: On remote road trips, I stop for gas at the first opportunity I have after my tank drops below half full. You never know when the next stop will be – better to keep the tank topped up!
Tolls On The Drive From Boston To Portland Maine
I-95 includes tolls, especially leaving Boston and entering Maine. In fact, I’ve never been anywhere that seems to have as many tolls as Boston.
Have an EZ-Pass or cash/card ready at toll booths. EZ-Pass is definitely preferable as tolls become cashless and un-operated.
If you’ve rented a car, many rental companies will pay the toll on your behalf and then charge you after. In my experience, they also like to hit you with a $25+ “convenience fee”… so you’re better off paying the tolls yourself if you can.
Wildlife Safety
You will probably spot deer along the roads, and possibly even moose or foxes. Wildlife is more likely at dawn or dusk. Stay alert while driving through forested areas, where it’s even more likely you’ll have a deer run out in front of you.
Having lived in my campervan for several years and traveled all of the US, I will say I’ve never seen as many deer in the roads as I do when I’m in the Northeast. If you see one deer, assume there are others close behind it and always slow down.
Optional Extensions For Your Boston To Maine Road Trip
If you have a bit more flexibility in your schedule or want to turn this Boston to Maine road trip into a 4- or 5-day getaway, here are a few options to make your trip even more memorable.
If you have a whole week check out this 7 day New England road trip itinerary which also includes Vermont and New Hampshire.
1. Camden and Rockland:
Between Portland and Bar Harbor, the towns of Camden and Rockland make for fantastic overnight or lunch stops. Camden is famous for its harbor views and hiking trails, while Rockland has an excellent art scene, including the Farnsworth Art Museum.
2. Moose Watching in Greenville:
Add an inland detour north from Bangor to Greenville for a moose safari. This area is quieter than the coast and offers a more rustic Maine experience.
3. Schoodic Peninsula (Acadia’s Quiet Side):
If Bar Harbor and the main section of Acadia feel too crowded, take the ferry or drive to the Schoodic Peninsula. It’s less developed, incredibly scenic, and has peaceful hiking trails like the Schoodic Head Trail.
4. Explore More of Boston:
If you’re flying into Boston, consider padding your itinerary with an extra day to explore the Freedom Trail, tour Fenway Park, walk around the North End, or take a day trip to Salem.
5. Lighthouse Trail:
Spend a little extra time chasing lighthouses along the coast—Nubble Light in York, Marshall Point Light near Port Clyde (featured in Forrest Gump), and Bass Harbor Head Light near Acadia are all worth the stop.
Keep Planning Your Boston To Maine Road Trip
Check out these additional resources to plan your road trip from Boston to Maine!
