Maine’s Great Outdoors Itinerary: From Rugged Coast to Wild Waterways
Maine’s Great Outdoors Itinerary
Start / End
Portland, Maine
States Covered
ME
STATES COVERED
Maine
PARKS COVERED
Wolfe’s Neck Woods State Park, Popham Beach State Park, Camden Hills State Park, Acadia National Park, Quoddy Head State Park, Katahdin Woods & Waters National Monument
SUGGESTED DAYS
11-14+
SUGGESTED SEASON
Spring, Summer, Fall
#ThisIsMyRoute
Overview
This outdoor-focused Maine itinerary follows the state’s natural rhythm, moving from the rocky coastline and island-dotted bays to inland lakes, forests, and the wild landscapes of northern Maine before looping back south. Designed for travelers who want to hike, paddle, and explore without skipping Maine’s food and small-town charm, this route works best over 10–14 days, with late spring through early fall offering the most flexibility. Enjoy a mix of national parks, state parks, scenic drives, and communities that make slowing down part of the experience.
This itinerary will start and finish in Portland, and with its options to fly, drive, or take the train, it’s an easy place to get to. Travelers from Boston and New York City can arrive by Amtrak, which offers a relaxed, scenic ride straight to within 10 minutes of downtown Portland, or by car in just a few hours. That ease of access makes Maine feel surprisingly close. Once you arrive, though, it quickly feels worlds away, setting the tone for a trip that balances convenience with true escape.
This itinerary was created in partnership with VisitMaine.com.
Maine’s Great Outdoors Itinerary
DAY 1: Portland, Maine
Begin your journey in Portland, where Maine’s coastal energy meets easy outdoor access. Start with stand-up paddleboarding or kayaking in Casco Bay. You’ll spend your time weaving between islands with views of working lobster boats and historic forts. If you’d prefer to be on the water without actually getting in, we’d recommend taking a ferry ride for some excellent bird, wildlife, and lighthouse watching.
On land, explore the city by bike along the Eastern Promenade Trail, which offers sweeping ocean views and a relaxed introduction to Maine’s outdoors. Afterward, refuel at Duckfat, Eventide Oyster Co., or Twelve for a farm-forward meal. For overnight stays, Portland offers everything from boutique hotels to charming inns, making it an ideal launch point.
DAY 2: Wolfe’s Neck Woods State Park & Freeport
23 miles/37 km, 30 minutes
Just north of Portland in Freeport, Wolfe’s Neck Woods State Park delivers one of Maine’s most accessible coastal hiking experiences with varied trails through forest, salt marsh, and along rocky shoreline overlooking Casco Bay. A great choice for your visit is the Harraseeket and White Pines Trail Loop. It’s a roughly two-mile (three kilometer) easy loop that combines peninsula forest paths with peaceful bay views. It’s ideal for a morning stretch or relaxed afternoon wander.
When hunger calls, head into Freeport’s town center for a bite or coffee: start your morning with a pour-over at The Coffee Maker at 31 Main or Isabella’s Café & Bakery for fresh pastries. Porter Kitchen + Bar is a local favorite for dinner with seasonal dishes and wood-fired pizzas, or grab a relaxed meal and craft beer at King’s Head Pub before settling in for the night.
If you’re staying overnight in the area, Wolfe’s Neck Center’s oceanfront campground and cabins offer a truly scenic place to rest right near the park with views across the bay and access to nature trails and activities. Otherwise, choose cozy lodging in downtown Freeport itself to be steps from shops and restaurants.
DAY 3: Popham Beach State Park & Bath
33 miles/53 km, 52 minutes
Set at the mouth of the Kennebec River, Popham Beach State Park offers wide sandy shores, shifting sandbars, and dramatic tides that make every visit feel different. It’s an ideal place for beachcombing, swimming, kite flying, or simply watching the surf roll in along one of Maine’s most beloved beaches. At low tide, wander toward Fox Island for a longer shoreline walk and expansive coastal views; at high tide, the beach becomes a more compact, energetic place to enjoy the ocean.
Just down the road in Bath, refuel at The Winnegance Restaurant & Bakery, a longtime local favorite known for hearty breakfasts, baked goods, and classic Maine comfort food, perfect after a salty beach day. For something more intimate and seafood-forward, The Lady Oyster offers a guided and memorable dining experience in nearby Phippsburg, centered around oysters, wine, and coastal flavors. (Pro tip: Lady Oyster is reservation only, so book in advance!). Before leaving town, take a few minutes to explore the area’s quiet charm by stopping into a local general store or keeping an eye out for seasonal roadside art stands and handmade goods from local makers. These often pop up during the warmer months.
DAY 4: Camden Hills State Park
64 miles/103 km, 1 hour, 30 minutes
Camden Hills State Park is one of the few places in Maine where mountains rise directly from the sea, creating a dramatic meeting point of forest, granite, and ocean. Start with a hike up Mount Battie, where a relatively short but rewarding climb delivers sweeping views over Camden Harbor, Penobscot Bay, and the island-dotted coastline beyond. For a longer, more immersive experience, venture deeper into the park on trails like the Megunticook or Maiden Cliff trails. These trails offer rugged terrain, quiet forest stretches, and elevated viewpoints that showcase Maine’s wild interior.
After a day on the trails, Camden’s compact downtown is just minutes away and feels like a natural continuation of the experience. Stroll the harborfront, browse locally owned shops and galleries, or relax by the water as sailboats drift in and out. When it’s time to eat, Long Grain delivers bold, Thai-inspired flavors that have earned it a loyal following. For an elevated dining, Natalie’s at the Camden Harbour Inn offers an experience that mirrors the area’s refined coastal charm. Together, Camden Hills and its surrounding town create one of Maine’s most seamless pairings of outdoor adventure and small-town culture.
DAY 5: Penobscot Bay Windjammer Cruise (Optional Add-On)
For a true Maine adventure, consider adding an overnight windjammer sailing trip from Camden or Rockland. These historic schooners offer a hands-on sailing experience, complete with island stops, swimming, and meals onboard. It’s a unique way to experience Penobscot Bay and adds a memorable, slow-travel element to the itinerary before continuing east.
DAY 6: Acadia National Park & the Blue Hills Peninsula
70 miles/ 113 km, 1.5 hours
No Maine outdoor itinerary is complete without Acadia National Park, where granite peaks, carriage roads, and rocky coastline define the landscape. Hike or bike the park’s iconic routes, catch sunrise from Cadillac Mountain, explore dramatic bayside trails like the Great Head Trail, or cruise along Park Loop Road to see Thunder Hole and Otter Cliff. For a change of pace, drive over to the Blue Hill Peninsula, where shoreline paddling, quieter forest paths, and views across Blue Hill Bay offer a peaceful complement to Acadia’s busier highlights.
After a day of exploring, sample what the peninsula has to offer beyond the trailhead. In Blue Hill itself, stop for coffee and pastries at Bucklyn Coffee or a relaxed lunch at Marlintini’s Grill. Art lovers will enjoy browsing local creativity at Handworks Gallery and Blue Hill Bay Gallery, while the Blue Hill Co-op offers regional foods and artisan goods that make great picnic additions. If you’re in the mood for something special, Arborvine provides a standout dinner with seasonal ingredients just a short drive from the park.
DAY 7: Quoddy Head State Park (Optional Add-On)
99 miles/159 km, 2 hours, 10 minutes
For travelers with extra time, continue east to Quoddy Head State Park, home to the easternmost point in the United States. Clifftop trails, bold ocean views, and a historic lighthouse make this a rewarding detour. Wildlife sightings and fewer crowds add to the feeling of reaching Maine’s far edge, offering a dramatic shift from the busier southern coast.
DAY 8: Katahdin Woods & Waters National Monument & Millinocket
127 miles/204 km, 2 hours, 40 minutes from Acadia National Park
Heading deep into northern Maine, Katahdin Woods & Waters National Monument offers a quieter, more remote counterpart to Baxter State Park, with vast forests, river corridors, and trails framed by views of Mount Katahdin. Designated an International Dark Sky Sanctuary, the monument is also one of the best places in the Northeast for stargazing. Here, clear nights reveal skies largely untouched by light pollution.
Millinocket makes an ideal base for exploring the area, striking a balance between access and comfort after days spent hiking or paddling. There are plenty of lodging options in the area, but one of our favorites is the welcoming 100 Mile Wilderness Inn, a stylish, town-based option for travelers looking to recharge. In the evenings, refuel at local favorites like Knife Edge Brewing, where craft beer and hearty meals provide a relaxing end to the day.
DAY 9: Greenville & Moosehead Lake Region
58 miles/93 km, 1 hour, 40 minutes
The Moosehead Lake area feels like classic North Woods Maine: vast water, quiet forest edges, and a sense of wild space that invites slow mornings and active days. Spend your time canoeing or boating on the state’s largest lake, hiking nearby trails, or simply enjoying the stillness of the water. Greenville and the surrounding towns offer easy access to outdoor outfitters like Northwoods Outfitters Moosehead Lake for gear or guided activities, making this a comfortable and adventure-rich stop.
When it’s time to eat, Kelly’s Landing is a local favorite for lakeside seafood with scenic views, perfect for a memorable dinner after paddling or boating. For lodging, consider the boutique charm of Greenville Inn at Moosehead Lake or the cozy comfort of Kineo View Lodge, both offering warm stays near town and lake access. Art lovers and gift hunters will enjoy browsing local handcrafted items and nature-inspired pieces at shops around Greenville. There are plenty of galleries and boutiques that reflect the region’s creative spirit.
DAY 10: Waterville
79 miles/127 km, 1 hour, 40 minutes
Set along the Kennebec River, Waterville offers that quintessential New England feel with brick buildings, historic storefronts, leafy streets, and a strong sense of local pride. It’s a college town at heart, home to Colby College, which brings an unexpected layer of arts and culture to the area. The Colby College Museum of Art is a standout stop, with an impressive collection that rivals big-city museums and a beautifully landscaped campus that’s lovely to wander.
Downtown Waterville is compact and walkable, making it easy to pop into locally owned cafés, bookstores, and small shops. It’s an ideal place to slow down for an afternoon: grab a coffee, stroll along the river, and soak up the small-town rhythm before continuing on your journey. Waterville works well as a cultural pause between outdoor-heavy destinations. It’s grounded, welcoming, and distinctly Maine, with that classic New England charm woven into everyday life.
DAY 11: Return to Portland
75 miles/121 km, 1 hour, 15 minutes
End your journey back in Portland, where you can revisit favorite restaurants, explore more of the Old Port, or take a final sunset walk along the waterfront. It’s a fitting place to reflect on a trip that moved from rugged coastlines to deep wilderness and back again.