Why Boothbay Harbor, Maine, Is the Best Getaway from Chicago

If you’re feeling overwhelmed, stressed, and burnt out, it’s time for a change of pace. Take a break from the city life with some fresh air, ocean views, and the perfect balance of outdoor activities and relaxation. The ideal getaway from Chicago is in the small oceanside town of Boothbay Harbor, Maine! Perched on top of a hill and overlooking the gorgeous harbor, Topside Inn offers an enchanting escape you won’t find anywhere else. To start planning your getaway today, take a look at our complimentary Vacation Guide. Inside you’ll find everything you need to plan a weekend getaway you’ll never forget! 

Request the Vacation Guide 

The Ultimate Trip: A Getaway from Chicago to Boothbay Harbor, Maine 

Early Morning: Indulge in a Delicious Breakfast 

It’s true what they say: Breakfast is the most important meal of the day! The best way to start your weekday or weekend getaway from Chicago is to wake up in Boothbay Harbor with a delicious breakfast at Topside Inn. This complimentary part of your stay includes ready-made favorites like yogurt, homemade granola, and fresh fruit, as well as freshly prepared, hot dishes like Lemon-ricotta pancakes with Maine blueberry compote and crisp, applewood-smoked bacon. For an even more magical experience, enjoy your breakfast and then head outside to watch the morning fog lift over our gorgeous harbor. You’ll have a front-row seat to the calming ocean views! 

Early Afternoon: Get Some Retail Therapy in Downtown Boothbay Harbor 

If unique shops with small-town charm are your cup of tea, you’ll adore downtown Boothbay Harbor. This quaint area is just a few steps from our front door and offers an array of one-of-a-kind stores. It’s easy to spend an hour or two simply wandering through this petite town center, a cup of coffee (from a local shop like Red Cup Coffeehouse) in hand.  

Here are a few of our favorite local spots: 

Early Evening: Dine at Midcoast Maine’s Best Restaurants 

Of all the things to do during your visit to Boothbay Harbor, enjoying a delicious meal is a must! There’s no better way to get to know the area than to try the food that defines this region. From seafood restaurants dotted throughout downtown to upscale dining on the water, the best restaurants in Boothbay Harbor offer a little bit of everything! With no shortage of delicious meals, you’re sure to find a new favorite dish at any of these fantastic local restaurants:  

Get A Good Night’s Rest at Topside Inn! 

View of bedroom in Room 3 at Topside InnIf relaxation is the goal of your getaway from Chicago? Look no further than Topside Inn for your stay! At Topside Inn, our beautiful accommodations provide some of the best lodging in the area. They’re the perfect place to rest and recharge after a day full of exploring! No matter how you spend your days enjoying the area, a trip to Midcoast Maine is always a good idea. Topside Inn has everything you need to make it truly memorable, including breakfastgetaway packages, and special add-ons 

Ready to see a new side of Boothbay Harbor, Maine? Check our availability, and book your stay! We can’t wait to host you.