Boston to Bar Harbor Road Trip 🗺️ | Best Stops on Your Ultimate Coastal Itinerary

Embarking on a road trip from the historic city of Boston to the stunning coastal landscapes of Bar Harbor, Maine, is a quintessential New England experience. This journey offers a diverse tapestry of charming towns, picturesque beaches, cultural landmarks, and breathtaking natural beauty. This itinerary highlights some of the best stops along the way, allowing you to customize your trip based on your available time, whether you have 3, 5, or 7 days to explore.

Boston, Massachusetts – The Starting Point

Your adventure begins in Boston, a city steeped in history and brimming with modern attractions. Before hitting the road, dedicate some time to explore the highlights of this vibrant metropolis.

The Freedom Trail: Walk this iconic 2.5-mile red-brick path that leads you to sixteen significant historical sites, offering a glimpse into the American Revolution.
Black Heritage Trail: Discover the stories of Boston’s 19th-century African American community through this fascinating walking trail in Beacon Hill.
Union Oyster House: Indulge in fresh seafood at America’s oldest continuously operating restaurant, a Boston landmark since 1826.
Neptune Oyster: For a more contemporary oyster experience, head to this acclaimed North End spot known for its exceptional seafood.
Bova’s Bakery: Treat yourself to delicious Italian pastries at this beloved North End bakery, a local favorite.

Salem and Portsmouth – History and Coastal Charm

As you leave Boston, consider a stop in the bewitching town of Salem, Massachusetts, followed by the historic seaport of Portsmouth, New Hampshire.

Salem, Massachusetts: Where History Meets Mystery

Just a short drive north of Boston, Salem is famous for its rich maritime history and, most notably, the 1692 witch trials.

Salem Witch Trials Memorial: Reflect on the tragic events of the witch trials at this poignant memorial.
Bewitched Statue: Snap a photo with the statue of Elizabeth Montgomery as Samantha Stephens from the iconic TV show “Bewitched.”
Peabody Essex Museum: Explore diverse art and cultural collections, including maritime art and Asian export art.
Salem Maritime National Historic Site: Learn about Salem’s significant role in American maritime trade.

Portsmouth, New Hampshire: A Historic Seaport

Continuing north, you’ll arrive in Portsmouth, a charming city with a rich colonial history and a vibrant contemporary culture.

Strawbery Banke Museum: Step back in time at this living history museum that recreates life in a 10-acre waterfront neighborhood from the 17th to the mid-20th century.
USS Albacore Museum: Tour a real Cold War submarine and learn about its fascinating history.
Market Square: Stroll through the heart of downtown Portsmouth, filled with unique shops, art galleries, and restaurants.
Portsmouth Harbor Cruises: Enjoy scenic views of the harbor and the historic lighthouses.

Southern Maine – Beaches and Coastal Towns

Your journey continues into Southern Maine, a region renowned for its beautiful beaches, picturesque coastal towns, and delicious seafood.

Ogunquit: Beautiful Beach and Marginal Way

Ogunquit Beach: Relax on this 3.5-mile stretch of sandy beach, considered one of the finest in the Northeast.
Marginal Way: Take a scenic walk along this mile-long paved cliff walk offering stunning views of the rocky coastline.
Ogunquit Playhouse: Catch a performance at this historic theater that has hosted numerous stars over the years.

Kennebunkport: Coastal Charm and Lobster Rolls

Dock Square: Explore the vibrant heart of Kennebunkport, filled with boutiques, art galleries, and eateries.
Ocean Avenue: Take a scenic drive past stunning seaside homes, including the famous Bush compound at Walker’s Point.
Goose Rocks Beach: Enjoy the pristine white sands and gentle waves at this beautiful beach.
H.B. Provisions: Stop by this classic general store for local goods and treats.
Huttopia Southern Maine (Sanford): Consider an overnight stay at this unique glamping site offering comfortable wood and canvas tents.

Portland – Foodie Paradise and Historic Landmarks

Continue your journey north to Portland, Maine’s largest city, known for its vibrant food scene, historic architecture, and stunning waterfront.

Portland Head Light: Visit Maine’s oldest lighthouse, a picturesque landmark located in Cape Elizabeth, just a short drive from Portland.
Fort Williams Park: Explore the grounds surrounding Portland Head Light, offering beautiful coastal views and walking trails.
Old Port: Wander through the cobblestone streets of Portland’s historic waterfront district, filled with shops, restaurants, and bars.
Boone’s Oyster & Fish House: Indulge in fresh oysters and other seafood delights with waterfront views.
Luke’s Lobster: Savor a classic Maine lobster roll at this popular spot.
The Holy Donut: Try a unique potato donut, a Portland specialty.
Eastern Promenade: Enjoy panoramic views of Casco Bay from this scenic trail and park.
Casco Bay Islands: Take a ferry to explore the charming islands of Casco Bay, each with its own unique character.

Maine’s Midcoast – Scenic Harbors and Coastal Beauty

As you continue north, you’ll enter Maine’s Midcoast region, famous for its rugged coastline, charming harbors, and picturesque towns.

Boothbay Harbor: A Quintessential Maine Town

Coastal Maine Botanical Gardens: Explore these stunning gardens featuring diverse plant collections, walking trails, and whimsical troll sculptures.
Cabbage Island Lobster Bake: Experience a traditional New England lobster bake on a scenic island.
Boothbay Harbor Land Trust Trails: Hike through the region’s natural beauty on the numerous trails maintained by the Land Trust.
Maine State Aquarium: Discover local marine life at this family-friendly aquarium.

Rockland: Art, Lighthouses, and Windjammers

Farnsworth Art Museum: Admire a significant collection of American art, including works by the Wyeth family.
Rockland Breakwater Lighthouse: Walk along the nearly mile-long granite breakwater to reach this historic lighthouse.
Owl’s Head Lighthouse: Take a short drive to this picturesque lighthouse offering panoramic views of Penobscot Bay.
Maine Lighthouse Museum: Explore the largest collection of lighthouse artifacts in the United States.
Windjammer Cruises: Experience the thrill of sailing on a historic windjammer in Penobscot Bay.

Camden: Stunning Harbor Views and Hiking

Camden Harbor: Admire the beauty of this picturesque harbor dotted with sailboats and windjammers.
Mount Battie: Drive or hike to the summit of Mount Battie in Camden Hills State Park for breathtaking panoramic views of Penobscot Bay.
Camden Hills State Park: Explore over 30 miles of hiking trails offering various levels of difficulty and stunning coastal vistas.
Curtis Island Light House: View this charming lighthouse from the harbor or during a sailing tour.

Bar Harbor and Acadia National Park – The Grand Finale

Your final destination is Bar Harbor, a charming town nestled next to the majestic Acadia National Park.

Bar Harbor: Gateway to Acadia

Downtown Bar Harbor: Explore the shops, restaurants, and art galleries in this charming coastal town.
Shore Path: Take a leisurely stroll along the scenic Shore Path, offering beautiful views of Frenchman Bay.
Stewman’s Lobster Pound: Indulge in fresh Maine lobster with stunning waterfront views.
Bar Island Land Bridge: During low tide, walk across the sandbar to Bar Island, part of Acadia National Park.

Acadia National Park: Nature’s Masterpiece

Park Loop Road: Drive this scenic 27-mile road, stopping at various overlooks and trailheads to experience the park’s beauty.
Cadillac Mountain: Drive or hike to the highest point on the Eastern Seaboard for breathtaking sunrise or sunset views.
Jordan Pond: Hike the scenic Jordan Pond Path and enjoy tea and popovers at the Jordan Pond House.
Great Head Trail: Hike this moderate trail offering stunning coastal views and dramatic cliffs.
Sand Beach: Relax on this unique beach nestled between granite mountains, composed of shell fragments.
Thunder Hole: Experience the roar of the ocean as waves crash into this unique rock formation.
Carriage Roads: Explore over 45 miles of historic carriage roads perfect for biking and leisurely strolls.

This itinerary offers a wealth of possibilities for your road trip. For a 3-day trip, you might focus on Boston, Portland, and a brief overview of Acadia/Bar Harbor. A 5-day journey could allow for more in-depth exploration of Portland, the Midcoast (perhaps choosing between Boothbay Harbor, Rockland, or Camden), and Acadia/Bar Harbor. With 7 days, you can comfortably visit all the suggested stops and spend more time enjoying each location and its unique attractions. Customize this guide to create your perfect Boston to Bar Harbor adventure!

Summary of Best Stops:

Location	Highlights	Activities
Boston, MA	Freedom Trail, Black Heritage Trail, Historic Restaurants	Walking tours, exploring historical sites, dining
Salem, MA	Witch Trials Memorial, Bewitched Statue, Maritime History	Visiting historical sites and museums, ghost tours
Portsmouth, NH	Strawbery Banke Museum, USS Albacore, Market Square	Exploring historic sites, shopping, dining, harbor cruises
Ogunquit, ME	Ogunquit Beach, Marginal Way, Ogunquit Playhouse	Beach relaxation, scenic walks, theater performances
Kennebunkport, ME	Dock Square, Ocean Avenue, Goose Rocks Beach	Shopping, scenic drives, beach activities
Portland, ME	Portland Head Light, Old Port, Eastern Promenade, Casco Bay Islands	Exploring historic sites, dining, island hopping, enjoying coastal views
Boothbay Harbor, ME	Coastal Maine Botanical Gardens, Lobster Bakes, Land Trust Trails, Maine State Aquarium	Exploring gardens, enjoying lobster bakes, hiking, visiting the aquarium
Rockland, ME	Farnsworth Art Museum, Rockland Breakwater Lighthouse, Owl’s Head Lighthouse, Windjammer Fleet	Visiting art museums, exploring lighthouses, sailing
Camden, ME	Camden Harbor, Mount Battie, Camden Hills State Park	Enjoying harbor views, hiking, scenic drives
Bar Harbor, ME	Downtown Bar Harbor, Shore Path, Bar Island Land Bridge	Exploring the town, scenic walks, exploring Bar Island during low tide
Acadia NP, ME	Park Loop Road, Cadillac Mountain, Jordan Pond, Great Head Trail, Sand Beach, Thunder Hole, Carriage Roads	Scenic driving, hiking, biking, enjoying coastal scenery, picnicking