The Best Travel Itinerary for All Visitors in Freeport, Maine

Whether you're here for the shopping, the seaside charm, or the local eats, The Harraseeket Inn is your cozy and convenient home base in the heart of Freeport. We've curated the ultimate collection of itineraries for every type of traveler — from weekend wanderers to foodie families and everything in between. Dive into the best of Freeport and let your Maine adventure begin.

For The Adventurers:

A Day Filled with Coastal Adventures.

Morning:

• Explore the trails at Wolfe’s Neck Woods State Park and soak up the picturesque nature of Casco Bay.

Midday:

• Swing by Wolfe’s Neck Center – a living coastal farm. During the summer – kayak, canoe, and bicycle rentals are available daily through their oceanfront campground

Evening:

• End the day with a sunset kayak trip in Casco Bay from the L.L. Bean Flying Point Paddling Center.

Trails + Hikes + More.

Morning:

• Hike the scenic trails and enjoy panoramic views at Bradbury Mountain State Park, located a short 15-minute drive north of Freeport.

Midday:

• Discover how sand dunes were formed in the middle of a lush Maine forest at the Desert of Maine. Recently renovated in 2022, the Desert features a new mini golf course, outdoor exhibits, and facilities.

Evening:

• Unwind and shop in Freeport Village, the popular hub for outlet stores. For dinner, relax and enjoy a delicious meal at Porter Kitchen + Bar.

For the Party of Two:

Easy-going Adventures.

Morning:

• Grab a coffee, smoothie, or enjoy a locally baked good from Sip House to start the day. From there, walk around downtown Freeport and window shop along Main Street – featuring charming village shops, outlets, and galleries.

Midday:

• Explore the Maine seacoast with your partner and book a couples kayak with Seacoast Tours of Freeport. Afterwards, head over to Love Point Oyster Farm for fresh oysters, a tour of Casco Bay, and soak in the beauty of Maine’s iconic coastline.

Evening:

• Unwind at The Harraseeket Inn around the outdoor firepit, and grab a s’mores kit from the front desk. For dinner, relax and enjoy a delicious meal at Porter Kitchen + Bar.

Go-With-The-Flow-Fun.

Morning:

• Sleep in and allow yourself to have a slow morning, you’re on vacation! Head downstairs for breakfast and order a classic Maine-favorite: a stack of blueberry pancakes from the kitchen.

Midday:

• Take a short drive up to Bradbury Mountain State Park for a gentle hike and sweeping views. Stop by Bow Street Market and buy some snacks to share at the top.

Evening:

• Tap into your creative side and visit Sea Love, a candle bar and boutique located downtown. Create a signature fragrance together to memorialize your Freeport vacation together! Afterwards, head to Mast Landing Brewing Company for a locally-crafted brew & delicious bites.

For The Family Pack:

Adventures for All.

Morning:

• Head to Wolfe’s Neck Center for a peaceful, walkable farm tour where you can meet friendly goats, watch the chickens roam, and explore scenic trails that go through pastures, forests, and shoreline—perfect for curious kids and nature-loving grownups alike.

Midday:

• Sign up for a family-friendly program at L.L.Bean’s Outdoor Discovery School—such as beginner kayaking, archery, or fly-casting. Afterward, grab a laid-back lunch at Linda Bean’s Kitchen & Topside Tavern—perfect for sandwiches, pizza, and Bean family recipes.

Evening:

• Wrap up the day with a stroll through downtown Freeport, where little legs can wander and curiosity runs free. Stop by Derosier’s or Ben & Jerry’s for a scoop of ice cream, then head to The Harraseeket Inn for a night in with board gam fun!

Oceanside Wonders Await.

Morning:

• Wake up and start the day with breakfast in Porter Kitchen + Bar. Order a classic Maine-favorite: a stack of blueberry pancakes!

Midday:

• Find a quiet stretch of shoreline at Winslow Park and spend the afternoon hunting for seashells and glimmering pieces of sea glass. It's a peaceful way to spark curiosity, slow down, and enjoy the simple beauty of the Maine coast.

Evening:

• As the day winds down, enjoy a relaxed family dinner at Tuscan Brick Oven Bistro—a local favorite. After dinner, cap off the evening with a splash in the indoor heated pool. It’s the perfect way for kids to burn off any last bits of energy before winding down for the night.

No matter what kind of traveler you are, Freeport has something special in store for you. Use these itineraries as a guide — or create your own adventure. When you're ready to unwind, The Harraseeket Inn will be right here to welcome you home!