Kick off your Maine adventure with the ultimate Boston to Moosehead Lake road trip in Greenville Maine! These are our must-see stops along the way.

A sunrise view of Moosehead Lake with smooth glassy water and pink color in the sky

🦞 1. Portsmouth, New Hampshire (1 hour from Boston)

  • Stroll through Market Square with its charming shops and cafés.
  • Grab fresh seafood at Row 34 or enjoy a lobster roll with harbor views.
  • Explore Prescott Park for beautiful riverside gardens.

🧀 2. Kennebunkport, Maine (1.5 hours from Boston)

  • Visit the scenic Cape Porpoise Pier for iconic Maine coast views.
  • Stop for a lobster roll at The Clam Shack, a local favorite.
  • Walk along Dock Square for charming shops and galleries.

🫐 3. Portland, Maine (2 hours from Boston)

  • Explore the cobblestone streets of the Old Port District.
  • Savor a pastry from The Holy Donut (made with Maine potatoes!).
  • Visit Portland Head Light, Maine’s oldest lighthouse, for stunning ocean views.

🏞️ 4. Freeport, Maine (2 hours 20 minutes from Boston)

  • Stop at the flagship L.L. Bean Store, open 24/7.
    • QUIRKY SELFIE OPP: Giant L.L. Bean Boot – Freeport, ME
      • Outside the flagship L.L. Bean store stands a 16-foot-tall replica of their iconic boot, perfect for a fun photo op.
  • Enjoy a quick hike at Wolfe’s Neck Woods State Park.
  • Grab a lobster roll at Harraseeket Lunch and Lobster.
  • QUIRKY SELFIE OPP: Desert of Maine – Freeport, ME
    • A 40-acre expanse of glacial silt mistaken for desert sands, offering guided tours and a unique natural history.

🐻 5. Augusta, Maine (3 hours from Boston)

  • Tour the beautiful Maine State House, rich in history.
  • Visit the Viles Arboretum, a lovely spot for a nature walk.
  • Stop for a bite at The Red Barn, known for their seafood baskets.

You’re halfway through your ultimate road trip from Boston to Greenville, Maine.

🌲 6. Skowhegan, Maine (3.5 hours from Boston)

  • Walk the Skowhegan Riverwalk along the Kennebec River.
  • Stop for fresh baked goods at The Bankery.
  • Explore the Maine Grains Mill for organic flours and local products.

*QUIRKY SELFIE OPP: Perry’s Nut House – Belfast, ME

Visit this classic roadside attraction since 1927, featuring an eclectic mix of curiosities, taxidermy, and delicious homemade fudge.

*QUIRKY SELFIE OPP: Andre the Seal Statue – Rockport, ME

A heartwarming tribute to a harbor seal that became a local celebrity in the 1970s, commemorated with a charming statue.

*QUIRKY SELFIE OPP: Flying Moose – Rockwood, ME

A whimsical sculpture of a moose with wings, offering a quirky photo opportunity on Route 15 between Greenville and Rockwood.

You’ve arrived at your destination on your ultimate Boston to Moosehead Lake road trip!

A dusky view of Moosehead Lake with calm water and trees bordering it

🦌 7. Moosehead Lake Region (4.5 hours from Boston)

  • Explore Lily Bay State Park for lakeside picnics.
  • Take a moose safari for a true Maine experience.
  • AT LAST… Check into your cozy room at Lodge at Moosehead Lake, where adventure meets relaxation. This isn’t just a place to stay; it’s an experience. With its upscale elegance, unparalleled views of Moosehead Lake, concierge services, and a curated selection of adventures, the Lodge offers a gateway to the heart of Maine’s wild beauty.
  • MOOSE SAFARI: No trip to Moosehead Lake is complete without attempting to spot the region’s most iconic resident: the moose. The Lodge’s Moose Safari is a must-do for any wildlife enthusiast. The Northwoods of Maine are considered by many to be the best Moose viewing in the world; enjoy a private truck journey to remote mountain locations where a Maine Guide will help you explore the natural resources of the area.

    CALL OF THE WILD: For those seeking a deeper dive into the Maine wilderness, the Lodge’s “Call of the Wild” package offers a comprehensive adventure. Spend 8 hours with their exclusive private Registered Maine guide. Travel by vehicle with their guide to private and remote locations or include canoeing and/or hiking to areas frequented by our famous moose.
  • LAND, LAKE & AIR: The lodge’s Land, Lake & Air package is the ultimate in Maine adventure. Over the course of four days you will take an exhilarating seaplane ride over Moosehead Lake, spend 8 hours on our Call of the Wild excursion, travel across the lake on our beloved steamship Katahdin, and hike glorious Mount Kineo with a gourmet lunch prepared by the culinary team at 368 Maine Restaurant. It’s a one in a lifetime bucket list trip you don’t want to miss.

    While the outdoor adventures are a major draw, the Lodge itself offers a sanctuary of tranquility that you don’t want to miss.
  • Stunning Views: Every room boasts breathtaking views of Moosehead Lake, providing a constant connection to the surrounding beauty.
  • Upscale Elegance: The Lodge’s interior is a masterpiece of charm, featuring original 1917 restoration, cozy fireplaces, and luxurious suites.
  • Fine Dining: Enjoy delicious meals prepared with locally sourced ingredients at one of our Chef’s Tasting Dinners at 368 Maine Restaurant.
  • Relax and Unwind: After a day of adventure, unwind in the Lodge’s comfortable common areas or enjoy a relaxing soak in a jetted tub.

The ultimate drive from Boston to Moosehead Lake is more than just a journey—it’s an adventure! Take your time, enjoy the stops, and make unforgettable memories along the way!