Jessie's Supper Club Information

Tucked away along 2 Wolf Pond Rd in Owls Head, Jessie's Supper Club feels like stepping into a cozy, welcoming retreat where every detail seems designed for comfort and enjoyment. From the moment you walk in, the atmosphere strikes a perfect balance between relaxed charm and a touch of rustic elegance-soft lighting, polished wood accents, and tables that invite lingering conversations make it clear this is a place meant for savoring both food and company. The service reflects that same warmth, with staff who are attentive without being intrusive, always ready with menu suggestions or a quick chat about local favorites.

The menu itself is a delightful mix of hearty classics and inventive dishes that keep things interesting. Whether you’re drawn to the perfectly seared steaks, fresh seafood, or flavorful vegetarian options, each plate shows a dedication to quality ingredients and thoughtful preparation. Portion sizes are generous, yet nothing feels overdone; presentation is simple but appealing, letting the flavors speak for themselves. The rotating specials often highlight seasonal produce or locally sourced ingredients, giving a sense of the region’s flavors while keeping the dining experience fresh every visit. And for those who enjoy a relaxed evening with drinks, the wine and cocktail selections pair beautifully with the menu, rounding out the meal with just the right touch.

What makes Jessie's Supper Club truly stand out, though, is the way it feels deeply connected to its community. Local reviews frequently mention the friendly familiarity of the staff and the sense that this is more than just a meal-it’s an experience. Families, couples, and even solo diners find themselves coming back not just for the food, but for the welcoming vibe and the care evident in every detail. Nights here are often accompanied by a quiet hum of conversation, occasional laughter, and the satisfying clink of glasses, creating a rhythm that’s both comforting and lively.

For anyone exploring Owls Head, this location offers more than just a meal-it’s a chance to slow down, enjoy thoughtful cooking, and soak in a warm, inviting atmosphere. From the thoughtful menu variety to the attentive service and the subtle charm of the setting, Jessie's Supper Club manages to create an experience that feels both special and effortlessly approachable, leaving a lasting impression that keeps diners planning their next visit.

Business Info

What People's Say About Place

So we wanted to try Wednesday’s Mexican night. Got there and it was packed so not so lucky. So the following week I made reservations for 8. Never has everyone in our group been completely happy with their meal and or service. Jessie did it. We went back a second time and we’re just as happy. Thanks for a great meal and service. We’ll be back.

Love Jessie's. Best food in the area and a small but good beer selection. Have always had great service as well.

Jessie's is a total life saver! We came 15 minutes before closing and she still served us and let us stay way past closing while our camp warmed up. The food is always amazing! We love the chill atmosphere and it is great to watch a game and have a warm drink there. Our go to spot!

Great food and service. Eggs Benedict at brunch was outstanding and the bloody Mary was fantastic! Others had omelettes pancakes and pulled pork sandwiches and everyone was very happy with their meals. Nice to find a great new restaurant in the area.

This was our first time eating at this restaurant since it changed ownership and it will not be our last time. Service was excellent. Warm pita triangles were served with fresh garlic and olive oil, very tasty. I started with the Caesar salad which was very good. For my entree, I had the lobster ravioli, which was stuffed with real lobster pieces and covered in a saffron sauce loaded with lobster pieces. This was , by far, the most delicious lobster ravioli I have ever eaten. My husband had the broiled haddock with red curry sauce and he said it was outstanding, probably the best haddock entree he has ever had! Eventhough, Jessie's Supper Club is over an hour's drive, we will definitely be back and often!

I went up for lunch! The owner were very nice and the food was delicious! I ordered the big salad with grilled chicken and cream of mushroom soup. My waitress Amanda she was amazing as well making sure I had everything I needed!

Went here for the first time after a rave review from a friend and let me tell you, it did not disappoint!!! Great menu, great service, feels like home cook meals. Had a great burger after a hike. And the bourbon selection I highly recommend stopping in if you’re in the area, or make the drive for a fun day.

Jessie's Supper Club