A Sweet and Savory Weekend in Maine: Solo Travel for Women

Let’s be honest for a moment: Maine just gets it. It doesn’t try too hard. It doesn’t rush you. And it never asks you to hike up a mountain before you’ve had coffee. For women over 50 embracing solo travel, that alone makes Maine a very appealing weekend getaway.

This is the kind of destination where you can wander at your own pace, eat dessert before dinner if you feel like it, and enjoy your own company without feeling awkward—or invisible. Maine is calm without being sleepy, charming without being cheesy, and filled with places that feel just right for traveling solo after 50.

This trip is part of my ongoing series on solo travel day trips, where I share easy, close-to-home getaways designed to help women feel confident traveling solo.

Yes, couples and families love Maine too (and for good reason), but this guide is written for the woman traveling alone—confident, curious, and fully in her “I’ll do what I want” era.

Why Maine Is So Good for Solo Travel After 50

Maine has a rhythm that feels especially friendly for solo travel. Towns are small and walkable, people are welcoming without being intrusive, and there’s zero pressure to pack every moment with activity. You can explore for an hour, sit by the water for another, and call it a very successful day.

For women over 50, Maine offers:

• Walkable downtowns that feel comfortable and safe

• Scenic drives instead of physically demanding adventures

• Plenty of bakeries, cafés, bookstores, and waterfront benches

• Inns and hotels that feel cozy—not chaotic

In short, Maine lets you enjoy solo travel without needing a recovery day.

Portland, Maine: Walkable Streets, Great Food, Zero Rush

If you’re planning a solo weekend in Maine, Portland is an excellent place to start. Once you park your car, you can happily forget it exists—which is always my goal when traveling alone.

The Old Port area is full of cobblestone streets, independent shops, galleries, and restaurants that don’t mind if you’re dining solo with a book, your phone, or just your thoughts. It’s lively enough to people-watch but relaxed enough to linger.

Solo-approved food stops:

• Eventide Oyster Co. for a brown butter lobster roll that will absolutely ruin you for all others

• Two Fat Cats Bakery, where whoopie pies are treated with the respect they deserve

• Old Port Candy Co., a place that makes you briefly consider mailing candy home to yourself

  
  

Where to stay: Portland has everything from cozy inns to stylish boutique hotels with harbor views. Summer rates can be higher, but the walkability and atmosphere make it worth it for a weekend getaway.

Kittery, Maine: A Sweet Little Detour

Kittery doesn’t always get top billing, but it’s a great first stop if you’re driving north. While the town isn’t entirely walkable, the downtown area is compact and easy to explore once you’ve parked.

The real highlight here is Yummies Candy & Nuts, which has been delighting visitors since 1986. I went in “just to look” and came out with enough candy to suggest I’d had a very emotional day. No regrets.

Where to stay: Budget-friendly and practical, Kittery is ideal for a low-key overnight stop or a gentle start to your Maine solo travel adventure.

Bar Harbor, Maine: Scenic, Charming, and Not Just for Hikers

Bar Harbor is one of those places that feels welcoming the moment you arrive—which is especially nice when traveling solo. The town is walkable, lively, and full of shops, cafés, and waterfront views that make wandering feel effortless.

Yes, Acadia National Park is nearby, and yes, it’s famous for hiking. But here’s the good news: you don’t have to climb anything to enjoy it. Scenic drives and gentle coastal paths offer plenty of beauty without the sweat.

Sweet stops worth your time:

• The Pink Pastry Shop, charming and delicious in equal measure

• Ben & Bill’s Chocolate Emporium, where blueberry ice cream tastes like summer in Maine

  
  

Where to stay: Bar Harbor can be a splurge, especially in peak season, but waking up to ocean air and coastal views makes it feel worth it for a solo weekend getaway.

Ogunquit, Maine: Beachy, Artsy, and Easygoing

Ogunquit feels like a place where time slows down a little—and that’s part of the appeal. It’s walkable, creative, and just the right amount of lively.

The Marginal Way offers gorgeous ocean views and is more of a peaceful stroll than a hike (my preferred definition of “outdoorsy”). It’s perfect for solo travelers who like fresh air without a fitness requirement.

Sweet stop: Harbor Candy Shop, an old-school favorite that’s been around long enough to know exactly what it’s doing.

Where to stay: Mid-range inns and B&Bs that feel cozy, welcoming, and refreshingly unpretentious.

Freeport & Rockland: Low-Key Stops With Big Personality

Freeport is known for shopping, but Wilbur’s of Maine Chocolate Confections deserves special mention. They’ve been making chocolates for decades—and yes, there’s a life-size chocolate moose. You don’t forget something like that.

Rockland adds an artsy coastal vibe with galleries, cafés, and Bixby Chocolate Factory, a woman-owned business crafting small-batch chocolate since 2011. If you can catch a tour, even better.

Both towns are easy additions to a Maine weekend getaway and work beautifully for solo travelers who prefer flexibility over fixed plans.

When to Visit Maine: Timing Makes a Difference

June through August is Maine’s peak season. Summer brings warm weather, lively towns, and everything in full swing—but also higher hotel rates, more crowds, and the need to plan ahead, especially in popular spots like Portland and Bar Harbor.

For many women over 50, September and October are the sweet spot. The weather cools down, the crowds thin out, and Maine’s famous leaf-peeping season turns even a simple drive into a scenic experience. Late September, in particular, feels calm, colorful, and wonderfully unhurried.

Explore Next

If you’re loving the idea of easy weekend getaways, be sure to check out my guide to solo travel in Rhode Island, another charming New England destination that’s ideal for traveling on your own.

A Quick Note About Couples and Families

While this guide focuses on solo travel for women over 50, Maine is also a great destination for couples and families. The difference is that Maine makes it just as easy—and comfortable—for women traveling alone to enjoy the same experiences without feeling rushed, overlooked, or out of place.

Maine is one of those destinations where solo travel feels easy, especially for women over 50 looking for a relaxed weekend getaway. You don’t need a packed itinerary or extreme adventures—just a car, a loose plan, and a willingness to enjoy things at your own pace.

Whether you’re wandering Portland’s cobblestone streets, sitting by the water in Bar Harbor, or enjoying candy you absolutely did not need, Maine has a way of making solo travel feel not just comfortable—but genuinely enjoyable. And honestly, that’s the best kind of trip.