When guests stay at Five Gables Inn, they often ask about the best day trips from Boothbay, Maine that showcase the authentic beauty and culture of coastal Maine. Just a scenic 20-minute drive north along Route 27, the historic village of Wiscasset offers an enchanting escape that perfectly complements your peaceful retreat at our Boothbay bed and breakfast.
Known as “The Prettiest Village in Maine,” Wiscasset presents a captivating blend of maritime history, artisanal experiences, and quintessential New England charm that makes it one of the most rewarding day trips from our bed and breakfast in Boothbay, Maine.
The Journey to Wiscasset
Your adventure begins as you leave the tranquil surroundings of our Boothbay bed and breakfast, winding through Maine’s picturesque countryside dotted with lobster shacks, weathered barns, and views of the Sheepscot River as you cross the bridge into Wiscasset. The drive itself becomes part of the experience, offering that slow, contemplative pace that draws visitors to our corner of Maine.
As you approach Wiscasset, the village reveals itself gradually – first the iconic steeples piercing the skyline, then the elegant Federal and Colonial homes that line the tree-shaded streets, each telling stories of Maine’s prosperous maritime past.
Exploring Historic Wiscasset
Wiscasset’s compact downtown invites leisurely exploration on foot.
- Castle Tucker was built in 1807 for a prominent shipping family. It features three generations worth of family possessions. Tours are available Fridays, Saturdays, and Sundays from June through October.
- The Nickels-Sortwell House is a federal-style mansion also built in 1807. The historic barn serves as the visitor center for this residence turned hotel turned summer home. Tours are available Fridays, Saturdays, and Sundays from June through October.
- The 1811 Wiscasset Old Jail is one of the oldest remaining jails in New England. A unique thing about visiting here is learning about the difficult life for a jailer’s family. Docents lead tours on Saturdays and Sundays from Memorial Day until Indigenous Peoples Day.
- The Wiscasset Ancient Cemetery has tombstones from the 18th and 19th centuries and lovely views of the water.
- The Wiscasset Public Library is the oldest continuous circulation library in the country. It is housed in a building that was originally built to be a bank in 1805.
Artisanal Maine Cheese Tasting and Class in Wiscasset
One of the most delightful culinary experiences awaiting visitors is participating in an Artisanal Maine Cheese Tasting and Class. Maine boasts more than 80 licensed cheesemakers known for their innovation and quality. This class introduces participants to six of the best creameries in Maine.
During these immersive sessions, participants learn about the traditional cheese-making process, alongside the history and culture of Maine cheeses, while sampling an array of locally crafted cheeses. You will learn how the salt air, native grasses, and time-honored techniques contribute to the unique flavors that distinguish Maine cheese from their counterparts elsewhere.
If you take the class early in your Maine getaway, you can use the information you learn to guide other parts of your trip. The class host is happy to share recommendations for other cheese and agritourism stops along the way.
These cheese experiences perfectly embody the farm-to-table philosophy that defines much of Maine’s culinary landscape, connecting visitors directly with local producers and the land that sustains them.
Dining Delights
Wiscasset’s dining scene reflects the village’s commitment to showcasing local ingredients and traditional Maine flavors.
- Water Street Kitchen and Bar overlooks Sheepscot River. The menu features paella, lobster risotto, and steak frites.
- Red’s Eats is famous throughout New England for its lobster rolls, draws long lines of devoted fans who insist the wait is worthwhile.
- Panacea is a chowder house with a focus on comfort food.
- Head to Back River Bistro on a Monday for a lobster bake on the patio (this is a ticketed event).
- Aekeir Brewing has an ever-changing list of seven beers in the taproom. While they do not serve food, they are a fun addition to your brewery tour of the area.
Shopping Opportunities
The village’s antique shops and boutiques provide excellent browsing opportunities.
- The Wiscasset Antiques Mall is a group of nearly 100 dealers over three floors of shopping.
- Rock Paper Scissors has housewares, jewelry, craft supplies, and handmade stationery. It’s a one stop shop for whimsical things of beauty.
- The Wiscasset Bay Gallery features 18th-20th century American and European paintings. There are monthly exhibits for contemporary New England and Maine art.
- The Butterstamp Workshop houses two workshops and a showroom of buttermold products and beeswax ornaments.
Outdoor Adventure
If you are looking for something totally different to do, try Monkey C Monkey Do. The aerial adventure and zip line park will test your balance and your bravery.
Planning Your Perfect Day Trip
Most guests from bed and breakfasts in Boothbay find that a full day in Wiscasset provides the perfect balance of activities without feeling rushed. Consider starting your morning with a stroll through the historic district, followed by the cheese tasting experience, lunch at one of the local eateries, and afternoon browsing in the shops and galleries.
The beauty of day trips from Boothbay, Maine lies in their accessibility and variety. Wiscasset offers a different perspective on coastal Maine life – more intimate than larger tourist destinations, yet rich with cultural and culinary experiences that create lasting memories.
As you return to Five Gables Inn in the evening, you will carry with you the flavors of artisanal cheeses, images of historic architecture, and the peaceful satisfaction that comes from discovering one of Maine’s most charming villages. This perfect day trip exemplifies why so many guests return year after year to our bed and breakfasts in Boothbay – not just for the comfortable accommodations, but for the gateway they provide to authentic Maine experiences just waiting to be discovered.
Whether you’re planning your first visit or returning as a seasoned Maine traveler, Wiscasset represents the very best of what makes this region so special – a place where history, artisanal craftsmanship, and natural beauty converge to create unforgettable memories.
