This was originally published in 2016 on Little Lake County and has been updated to reflect current information.
Gentlemen! This post is for you…
Keep it down! I, along with all women, can hear you grumbling. We know that Valentine’s Day is not most men’s favorite holiday. We know you’ve called it a scam, a Hallmark holiday, and told us that you would rather spend the day with your ex…box 360. But I have some news for you: the celebration of Saint Valentine on February 14th began in the fifth century and has grown steadily since…it’s here to stay. It’s time for you to embrace it and take the opportunity to show your amazing wife how much you appreciate all she does for you and your family.

Put your complaints away men, you are already getting lucky because I have put together a few fun date night ideas in McHenry County that will make it look as though you thought ahead, did research and very carefully planned out an incredible night, when all you really had to do was read this article and make a reservation or two. You are welcome.
Date Night Ideas in McHenry County
Algonquin – The Traditional Date Night
Easy peasy.
Go to one of my favorite restaurants ever and an incredible date night spot in McHenry County: Montarra Grill. This culinary oasis is always a home run with its cool, trendy vibe and diverse menu. Several small plate options are available so you can share tapas-style, and even feed each other if you really want to make your wife googly-eyed and your table neighbors nauseated. For the bigger (and shyer) appetites, the steaks and larger entrees will not disappoint.

To make the night your traditional dinner and movie date, head over to the AMC Lake in the Hills Theater – two miles away – to catch a new release while sitting in comfy, adjustable (and pre-reserved) recliners. If you still have the energy to burn, head to the new Woods Creek Tavern or The Village Vitner down Randall Road for an after-dinner glass of wine or beer, both made in-house.
- Montarra Grill
1491 S Randall Rd, Algonquin | (847) 458-0505 - AMC Lake in the Hills Theater
311 Randall Rd, Lake in the Hills | (847) 458-5040 - Woods Creek Tavern
251 N Randall Road, Lake in the Hills | (224) 256-2063 - The Village Vitner
2380 Esplanade Drive, Algonquin, IL | (847) 658-4900
Crystal Lake – The Fun Date Night
Start your date with a good old-fashioned game of bowling in Crystal Lake’s vintage alley, Metro Bowl. If you bowl anything like I do, this is sure to start the night out with some laughs and possibly even ease the tension of the Valentine’s card you forgot to buy

Do some window shopping in the variety of downtown shops as you make your way down the street until you reach da Baffone Cucina Italiana, Crystal Lake’s premier Italian restaurant. This warm little family-owned spot offers traditional Southern Italian cuisine and will surely make you loosen your belt.

After over-indulging, walk across the street to Duke’s Alehouse for some good conversation and entertainment. Grab a craft beer from Duke’s extensive list, and relax together. Typically a jazz duo plays on Thursdays, Karaoke is on Fridays, and Saturdays feature a live band, so choose your date night according to your musical inclinations.
- Metro Bowl
77 Brink Street, Crystal Lake| (847) 458-0505 - Da Baffone Cucina Italiana
111 North Main Street, Crystal Lake | (815) 893-6149 - Duke’s Alehouse
110 North Main Street, Crystal Lake | 815-356-998
McHenry – The Cultural Date Night
To get your cultural juices flowing, head to McHenry for your Valentine’s night out. Voted the best Thai restaurant in McHenry County in 2015, the Green Peapod is a delicious way to impress your spouse. Be adventurous; try something new and show your partner that you can think outside of the pizza box.

After dinner, head to The Studio Art School for a painting class. Every Friday and Saturday night, different paintings are featured and taught to you in an easy step-by-step format; you leave with a bona fide masterpiece. Classes run from 7:00 p.m. – 9:30 p.m., and since you will both be painting the same portrait, you can hang one over your mantle, and give the other to your mother-in-law. Now you are even earning extra brownie points. (Am I good or am I good?)
- The Green Peapod
1225 N Green St, McHenry | (815) 578-9999 - The Studio Art School
3316 W Pearl Street, McHenry | (815)385-3990
Woodstock – The Romantic Date Night
Woodstock is so picturesque, it simply oozes romance. Begin your night at my favorite restaurant in the area, Mixteca. Delicious, homemade Mexican food and creative margaritas in a cozy space make this a winning choice. Don’t let the strip mall curb appeal fool you – the inside has a sexy ambiance.

After dinner, give your stomachs time to settle and head over to Woodstock Square. Walk around the historic piazza and listen to the classical music that is pumped through the gazebo speakers. If you are brave enough, ask your spouse to dance. I’m pretty sure she will eat that up, especially since your last dance may have been at your wedding.
Make your way to Read Between the Lynes, the indie bookstore in the square. Browse and enjoy the peace of being in a bookstore without your toddler throwing the merchandise off of the shelves and even sit still and breathe in the scent of an actual, non-electronic book for a minute. The store closes at 9:00 p.m. on Friday and Saturday nights, so leave enough time to enjoy.
If you want to go the extra mile, find a great book of poetry to read together at Ethereal Confections, your next stop just steps away. Find a spot in front of the fireplace or a bistro table in the back bar area to enjoy hot cocoa, coffee, beer/wine flights or spirits as you sample the gourmet chocolates and truffles.

- Mixteca
1390 S Eastwood Dr # B, Woodstock | (815) 334-8460 - Read Between the Lynes
111 E. Van Buren Street, Woodstock| (815) 206-5967 - Ethereal Confections
113 S Benton Street, Woodstock| (815) 687-0320
There you have it, your Valentine’s gift from me on a silver platter. Try one (or heck, try them all, there are four weekends in February) of these date nights, and I guarantee, you will not hear one complaint from your wife about another Valentine’s gone unnoticed while your neighbor’s husband flew her to Paris. (Besides, Paris is cold this time of year!)
What is your favorite date-night spot on Valentine’s Day?
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