Date Night Itinerary

After a day in the sun, a night on the town is waiting in Orleans.

Some couples trade sunshine for candlelight or moonlight, others are looking for live music and a crowded dance floor. No matter the style, Orleans can help set the mood for togetherness.

Night One - Tonight’s Special: Romance

Isn’t it romantic? The answer is “yes” at Captain Linnell House, an 1840s mansion offering several intimate dining rooms, Mahoney’s Atlantic whose fashionable and upscale dining will set the mood, and the Beacon Room, whose cozy ambiance features indoor and outdoor dining.

Delicious specialties and the romance of waterfront dining meet at the Orleans Waterfront Inn Restaurant while couples can toast each other with a Love Potion cocktail at the Double Dragon Inn.

Captain Linnell House

Night Two - The Big Screen

Enjoy a movie under the stars at the classic Wellfleet Drive-In Theatre, the last of its kind on Cape Cod and one of only about 300 left in the U.S. The drive-in is open Memorial Day through Labor Day, so when nights turn cool, try the Wellfleet Cinemas next door.

Dinner and movie are enjoyed together at the Chatham Orpheum Theater, whose onsite Orpheum Café serves appetizers and entrees along with beer, wine and cocktails.

Chatham Orpheum

Night Three

Long Walks on the Beach

End the day with a sundae at one of our many ice cream shops. Order your sweet treat to go and enjoy it during a spectacular sunset at the beach.

Nauset Beach on the Atlantic is open till midnight, so feel free to take your time on a stroll by the shore. Your romantic night by the sea ends by 10 p.m. at Skaket Beach on the bay side of Orleans, still plenty of time to walk hand-in-hand on the sand.

Sunset at Rock Harbor

Night Four - The Night is Young

Live music plays into the night at Hog Island Beer Co., the Barley Neck Inn and the Wellfleet Beachcomber. Cap off the night with a latte, smoothie or shake at the Hot Chocolate Sparrow, which stays open late during the summer.