Date Night in Fairfield

One town, so many options for a romantic evening. These themed outings represent a small sampling of things to do in and around Fairfield. Feel free to mix and match, and/or ask the hotel front desk for more suggestions.

Pool Sharks

For this date, you need to stay at The Circle.

1. You’ll start off at the famous Horseshoe in Southport. This local favorite has a jukebox, a wide variety of beers, bar food, darts, and pool. Play some cricket, have a burger, shoot a few games. Proper attire not required.

2. When you’ve had your fill of swimming in local dive bar nostalgia, head over to The Circle and change into your suits for a dip in the actual pool. It’s open till 8pm, and heated. Bring your own beverages. Sip, relax, repeat.

3. Speaking of swimming: this date ends with an optional viewing of Jaws on Netflix. Our Wifi is fast, not like many of the swimmers in this Spielberg classic, who do not make it to shore in time. Not to fear, you’re safe with us.

Say Cheese

1. The Fairfield Cheese shop offers all kinds of incredible cheese classes. They are educational, and entertaining.

Note: Watch the clock. You may need to pop next door to Harry’s for a bottle of wine before class, in the event they are closed afterwards. Thanks, CT blue laws.

2. After class, grab a few meats and cheeses of your choice. They offer a discount to attendees—the selection is outstanding.

3. Head to the Hi-Ho, grab a table on the upper balcony, and watch the moonrise (weather depending). Go ahead, gaze into each other’s eyes. Nothing cheesy about it.

Nature Calls

1. Head for a hike at the Aspetuck Land Trust, bring water, breathe deep. Optional add-ons: bugspray, gorp, binoculars, and a bird book. Warning: Ornithology can be cool, but also totally off-putting. Your call.

2. Head for dinner at Bloodroot in Black Rock. This totally vegan establishment is well-known for delightful food and a super unique atmosphere. They have books, cats, and lots of great vibes.

3. Go for a walk at St. Mary’s By The Sea. You’ll find plenty of roadside parking and lovely views of the Seaside Park Lighthouse and sunset. Might get breezy, so have a blanket, shawl, or other snuggle-ready device handy.

The Old Fashioned

Note: This date does not come with a 1957 Thunderbird, though a classic car is highly recommended. Our friends at the Southport Classic Car Gallery can help.

1. Head on over to Super Weenie, for a modern classic dinner. Nosh on famous hot dogs and french fries that will temporarily steal your date’s affections.

2. Rev the engine, head to Nutmeg Bowl and put everything into frame. You can choose a romantic theme option for your electronic scorekeeping, replete with animated chivalry. Optional disco upgrade: glow bowling.

3. Sunny Daes for old fashioned ice cream, on a cone, a bowl, or in a—you guessed it—sundae.