What to see
We have been visiting the beautiful town of Castine for the last 30 years. Located on a picturesque peninsula near Penobscot Bay, the town is close to the popular destinations of Blue Hill and Bar Harbor and has a charming, unique serenity. The wide, central ‘Main Street’ leads to the town pier, where you can grab a lobster roll from the Safe Harbor Cafe (5 Sea St, Castine) and watch the boats, from sailboats to dinghies, against the backdrop of the surrounding islands.
Don’t miss the Dice Head Lighthouse on the edge of town. The views are amazing and the color of the sky at sunset is truly magical. Lil’ Toot boat tours offer great excursions from Castine harbor. There are also several kayaking spots that we highly recommend as they are a great way to see hidden coves.
Castine has a rich architectural history, with homes dating back to the 18th and 19th centuries. The town features a variety of styles, from early colonial to stately Federal homes. Many of these historic buildings have been meticulously preserved and offer a glimpse into New England’s architectural heritage, including Redwood (circa 1885), La Rochelle (1903), and Martha Stewart’s mansion, Skylands (1925).
Acadia National Park near Bar Harbor is a must-do. This trail encompasses all of Maine’s natural beauty and wildlife, and you might even spot black bears. There are many different trails, but Cadillac Mountain is our favorite because it offers great views of the entire park. If you’re staying the night in the Mount Desert Island area, a trip to Pirate’s Cove Adventure Golf (70 First Street, Old Orchard) is a great way to have some fun. You don’t have to have kids to justify going; the lengthy 18-hole mini-golf course follows the fun and informative history of the famous pirates.
Where to shop
The biggest treasure is Blue Hill Wine Shop, a converted barn turned wine lover’s dream. Husband-and-wife team Max and Mary Treitler are Blue Hill natives and their shop stocks a carefully selected selection of cheeses and the best grocery items from around the world. The team can accommodate any wine request, whether it’s the best rosé for lobster or the perfect red for steak.
Compass Rose Bookstore is a charming bookstore with a wonderful selection of books, including a section dedicated to Maine authors (there are many!). Enjoy delicious coffee and refreshments while you browse. Meanwhile, Andre Strong is a bookstore specializing in diaries and journals, gardening, history, fine bindings, collected letters, travel, and literature related to Maine and New England.
Ronald Harte Antiques is the most eclectic shop filled with art, pottery, curiosities, lamps and furniture. A favourite with decorators and architects, this shop offers a unique selection perfect for adding character to any space.
Where to eat and drink
Arborvine remains true to its mission of providing the freshest, locally sourced foods. No matter the season, you can sample the best from regional farmers, fishermen, and foragers.
Trenton Bridge Lobster Pound (1237 Bar Harbor Rd, Trenton; ) is a must-visit food stop. Perfect for lunch on your way to Acadia National Park or dinner on your way back, this spot is located just off Route 3, just before Thompson’s and the bridge to Mount Desert Island. It’s a staple and a favorite with Bar Harbor locals. You can sit outside and pluck and pick your own lobster, always accompanied by a bag of Lay’s salty chips.
Our favorite restaurant in Downeast Maine is Sammy’s Deluxe, just outside Camden. The creative atmosphere is directly reflected in the food, with beautiful, playful expressions of Downeast Maine’s freshest ingredients. My personal favorites include the smoked haddock on pretzels and the halibut and beans in a green garlic and basil broth. The mismatched silverware and random assortment of plates add to the charm.
Tinder Hearth is a pizza shop away from the crowds, where you can sit in a magical garden full of wildflowers and enjoy thin crust pizza from a stone oven with a menu that changes daily. The place is so popular that you can only make reservations online on Monday mornings, and they sell out in minutes. And because it’s in Maine, there are oysters and fresh soft serve ice cream in the garden with waffle cones.
Perched on the cliffs above the beach on Deer Isle, Aragosta offers a delightful dining experience with beautiful coastal views. Known for its creative dishes that highlight fresh seafood and local ingredients, it is a favorite spot for locals and visitors alike.
Where to stay
Pentagöet Inn & Pub is a charming Queen Anne Victorian bed and breakfast nestled on a seaside cliff among stately elm trees on the central coast of Maine. The inn offers charming accommodations with views overlooking the historic village and harbor of Castine. Across from Pentagöet, grab a sweet treat, great coffee, and a hand-selected book from Compass Rose Bookstore.
The historic Castine Inn was built in 1898 and is located just a block from the water on Main Street, with its wraparound porch and stunning views of the harbor. I love having brunch at The Castine in its gorgeous dining room—it’s famous for its biscuits and hand-painted mural of the town.
Claremont is located near Acadia National Park in Southwest Harbor and offers stylish cabins, a heated outdoor pool, an on-site spa, plenty of dining options, and stunning views of Cadillac Mountain.