The 10 Best First Date Locations in Maine!

Finding that ideal spot for a first date can be challenging. You’re looking for a comfortable, public space that will take the pressure of those first-date nerves! Thankfully Maine has an abundance of awesome places across the state for first dates. From cozy coffee houses to delicious restaurants to tons of outdoor activities, you have plenty of chances to wow your date.

1. Union Restaurant, Portland, ME

Situated in the Press Hotel in Portland, the Union is one of the most buzzed about restaurants in Portland. Using only the finest local ingredients, the seasonal menus will leave your taste buds dancing all night long. Don’t miss the signature caramelized Brussels Sprouts as you’ve never had brussel sprouts so good! The staff is exceptional and the atmosphere is perfect for first date conversation. 

2. Pride’s Corner Drive-In, Westbrook, ME

Recently opened again after obtaining a digital projector, the Pride’s Corner Drive-In has been a favorite date spot since 1951. The drive-in can hold up to 550 cars and has a snack bar where you can purchase all your popcorn, soda, and candy needs. Each night there is always two movies. Get there early for the best spots!

3. Palace Playland, Old Orchard Beach, ME

What screams Hollywood movie first date than winning a stuff animal for your date? Palace Playland is fun for all ages. With rides, food, and tons of arcade games, you can have an afternoon of competitive first date fun in Old Orchard Beach. Loser buys the fried dough, right? 

4. Schooner Landing Restaurant, Damariscotta, ME

Every Friday starting at 4 p.m., the Schooner Landing Restaurant in Damariscotta hosts “Free Oyster Friday.” Yes, you read that right! Enjoy free oysters at their Dockside Bar along with live entertainment every Friday night. If you like reggae, blues, or R&B, head to Schooner Landing on Sundays for their All Pier Parties from 4 p.m. to 7 p.m.

5. Fort Williams Park, Cape Elizabeth, ME

Home to the most photographed lighthouse in America, Fort Williams Park is the perfect place for a picnic on a gorgeous summer afternoon. Either bring snacks from home or pick up any food from the many cafes and bakeries on your way there. Explore the old forts and enjoy the view of a classic Maine landscape.

6. Acadia National Park

If you live near Mount Desert Island then spending a day exploring Acadia National Park always makes for a great first date. From sunbathing at Sand Beach to tea and popovers at Jordan Pond House to hiking Cadillac Mountain, there is tons to do in Acadia National Park if you love the outdoors. 

7. Treworgy Orchards, Levant, ME

With fall just around the corner, why not bring your date to the corn maze and pick some delicious apples! The Paul Bunyan corn maze is sure to offer a few hours of fun. Afterwards you can pick some apples and a flower bouquet for your date at the pick-your-own flower bouquet fields. The Orchard also sells Gifford’s ice cream, pizza, and has a petting zoo. Treworgy Orchards is an affordable date option for college students, too!

8. Coastal Maine Botanical Gardens, Boothbay, ME

Opened from May through October, the Coastal Maine Botanical Gardens in Boothbay is a beautiful place for a first date, especially if your date loves flowers. If you’re a foodie, don’t miss their special “Kitchen Garden Dinner Series” with guest chefs throughout the season. Dress warm and enjoy the Gardens Aglow event in November through December where the Gardens is lit up with holiday lights. 

9. Portland Museum of Art, Portland, ME

The Portland Museum of Art in Portland boasts a large collection of American, European, and contemporary art from local and international artists. Spend an afternoon looking at the various art pieces and discussing each one with your date. If you’re looking to save a few dollars, the museum is free on Friday afternoons at 4 p.m. Afterwards, head over to the Top of the East for a glass of wine. 

10. Tumbledown Mountain

If both you and your date love the outdoors then hit the trails. Maine has thousands of miles of awesome hiking trails, but Tumbledown Mountain with its iconic summit pond is one of the best hikes in Western Maine. The 5.6-mile Tumbledown Mountain Trail is a great trail open year-round for hiking. You can celebrate your summit with a first date selfie!   

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