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.

🦞 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.
- QUIRKY SELFIE OPP: Giant L.L. Bean Boot – Freeport, ME
- 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!

🦌 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!