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Itinerary Alert: Not Your Average After Work Outing

We've all been there before - the end of work day stretch that has you eager for the day to be done but dreading going home and settling into the same old routine that will surely have morning and the start of the next work day rolling around in no time. To combat this feeling, we recently embarked on an after work outing that jam packed a whole day's worth of fun into a few short hours and still had us home in time to catch a full 8 hours rest before our alarm went off at 7:30am.

For us, the setting of this itinerary was an easy choice with our office situated on the cusp of Chelsea + the West Village, but the general template could be followed by most any area of New York, as outlined below, and it all starts with some mild advanced planning and the ability to wrap up your work day while the sun is still up. Grab a friend or a coworker and read on to discover the - not so average after work outing - we enjoyed and use the general basis to inspire your own post-work fun in the city.

Stop 1: Dinner + Drinks Near the Office

After a long day at work, you'll need to recharge with some body fuel. We recommend finding somewhere about 10 minute walk or less from the office to preserve time + energy, and thankfully, by New York's standards you can have hundreds of restaurants to choose from within a 10 minute radius of most any office spot in the city. If you're meeting a friend who works elsewhere in the city, another great option is to find a restaurant to meet at that's a ~10 minute walk from your last stop of the night so that you can centralize your plans to one location.

For us, we chose to dine with our favorite coworker at Cafeteria, an all day diner spot offering new-American meals and a light + airy ambiance. We loved that their entire storefront opened up to the outside on garage door tracks and gave us the opportunity to dine inside, without losing the fresh air + sunshine of a warm spring evening. The work day for us ends at 5PM and the restaurant is about an 8 minute walk from our office, so we proactively scored a reservation at 5:30 to give us some extra time but also ensure we wouldn't get stuck waiting and as planners, it would be remiss of us if we didn't encourage you to do the same. After a filling but not-too-filling meal (a BLAT sandwich and a mac and cheese spring roll) and a refreshing drink (a Pinot Grigio and a Spicy Passion Fruit Caipirinha) we were ready to head onto our next stop with time to spare.

Stop 2: Enjoy Golden Hour + Greenery With a Park Outing

After a long day of being cooped up in the office and then at dinner, we were itching to get outside and enjoy what was left of the beautiful spring day and a park outing ended up being the perfect stop in between our plans, and one that we highly recommend you add to your after work dinner plans. We've always been interested in exploring one of New York's newest public parks, Little Island, but had been discouraged by the idea of getting tickets to enter a public space - making this chunk of time between stops the perfect opportunity to take in golden hour and the park's greenery. As mentioned, Little Island does require timed entry tickets most days during the prime weather season but we were able to secure one for 7PM on the day of with no problem and at no cost (and truthfully we didn't see anyone checking tickets anyway). This gave us a full hour before show time to just enjoy being outside with unstructured plans.

The Little Island in particular was buzzing with picnicking people, live music at the amphitheater, flowers abloom and even a casual celebrity sighting of Matthew Gray Gubler. There were multiple sections for guests to explore, sit and take in the views and even different interactive musical instruments for public usage, making it a truly optimal place to stop for a little while, bask in the sun and people watch the people of New York. Even so, most any public park would've been a great way to break up the evening and get exposure to some greenery + fresh air and we even managed to squeeze in a trip to Pier 57's park as well.

As an added bonus for us, we were able to walk through the LEAF Festival on our way to the park - it was such a lovely and unexpected surprise to accompany our afternoon so we highly encourage you to do a quick Google search of any can't-miss events in your area before heading out for the day!

Stop 3: The Main Attraction

At the end of the day, we could have grabbed drinks anywhere after work and it probably would have been better than just going home, however, we were looking for something different to enjoy, which is how we found ourselves at City Winery's UpDating show. UpDating is unlike any show we've ever been to with the central premise being an audience-interactive show with two folks who are on an honest-to-God blind date (like literally, blind folded) at the center of the stage. Audience members text in questions for the blinded participants to be asked and the two hosts facilitate a comedy infused date between the daters and audience members. The entire thing was laugh-out-loud funny, cringe and wholesome all in one and the audience on the night we attended was filled with mostly 20-something year old women, making it an all around refreshing break from the norm. The entire process at City Winery made for a pleasant one with order-on-your-phone meals + drinks, friendly waitstaff and a beautiful venue space. The show started at 8 and was first come first seating - we got there around 7:40 and it ended up being the perfect time to arrive as we had most any seat in the house to choose from but had we come 15 minutes later we would've been squeezed into the back corner. The entire show lasted about an hour and 45 minutes and had us home by 10:30PM. Tickets for this show go for $25 a pop and sell out quickly, plus the show will be touring the country soon, so be sure to schedule a visit ASAP if you're interested in attending.

Though we had a lovely time at UpDating, any comedy or lighthearted show would have been an ideal setting for the third and final stop of this itinerary, and one that you should look to add to your own. The Stand, Poco, Route 66 Smokehouse and the many many many other NYC Comedy Clubs are all great places to look for affordable week day shows as well.

We hope that this itinerary template left you feeling inspired to create your own fun after work in whatever way energizes you. We have a number of additional unique after work plans that we'll be partaking in over the next few weeks and look forward to sharing those with you as well - be sure to subscribe and/or follow to stay up to date with all posts and recommendations and as always, keep putting a little disco in the details.


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