Day 1: Cruise along Route 1
Whether you follow this itinerary word for word or scope out your own spots along the way, you’ll find opportunities to hike, bike, kayak, camp, and just get outside. So before you get too far from Portland, pull over in Freeport and stock up on essentials at an iconic Maine store. You may think it’s all bean boots, but L.L. Bean’s flagship store has just about everything you could need while in the state, whether it's a sweatshirt to shield you from the ocean breeze or camping materials for the more daring -- plus it's open 24/7. Perfect packers should stop by too, because you’ll find freshwater aquariums and taxidermied bears, deer, and other animals inside. Plus, a giant version of the store’s popular boots -- an admittedly strange roadside attraction -- sits outside, where may even see the bootmobile drive by.
Mainers will aggressively defend their rights to the whoopie pie -- a dessert featuring dense chocolate cake rounds with frosting sandwiched between them -- from Pennsylvanians who naively think the dessert is theirs. So pick up whoopie pies for everyone in tow at Wicked Whoopies before embarking on a 45-minute drive to Wiscasset. The village is small, and when driving down Route 1 it may seem like every store you drive by is an antique shop. And that’s not too far off because the town is home to more than 30 antique stores including Lilac Cottage Antiques and the Wiscasset Antiques Mall that you should take your time going through.
Wrap up your trip at the spot that really put this town on the map: Red’s Eats. This place is a true lobster shack about the size of a minivan, and it’s no secret that they serve the best roll in the state. You’ll be glad you opted out of the pricey twin lobster dinner while you were in Maine’s big city, but be ready to wait in a line that stretches down the street.
You’ve spent the day eating Maine’s best food and prepping for the rest of your journey, so avoid falling into a food coma until you travel 45 minutes up the coast to Camden. There, you can spend the night in one of the many historic homes (think clawfoot tubs and sprawling gardens) that now house bed and breakfasts run by sweet locals, among them the Blackberry Inn.