#ValleyLoveMarket Peekskill Holiday Weekend Itinerary

Updated on

January 14, 2022

Visit the Valley Love Holiday Market and make a day of it in Peekskill with this guide.

For two weekends in December, we're hosting the Valley Love Holiday Market at Esther Place along with our friends POME florals and Bucko! The market features 30 rotating Hudson Valley vendors over the course of the four days with the goal of bringing fun back to Holiday shopping -- we want to offer something a little more personal (and local) than unboxing just another box from Amazon.

The Valley Love Holiday Market takes place on December 11, 12, 18, and 19 between 12 pm and 4 pm each day. What we want to do with this guide is provide an all weekend itinerary for a Holiday shopping getaway (or staycation) in Peekskill.

We're going to assume you're traveling to Peekskill by train and so the itinerary starts at the Peekskill Train Station on the Hudson riverfront.


9:05 am - Welcome to Peekskill! And aren't you lucky you've arrived in late 2021 because the once-abandoned train depot has been restored and is now The Central, a cozy and convenient coffee shop offering local Peekskill Coffee on brew and tasty sweet and savory snacks to stay or to go. To get in the holiday spirit we recommend the Peppermint Bark Latte and a delicious house-baked Sweet Cream Danish. Sit down and enjoy your light breakfast and the sound of the passing trains.

9:45 pm- Bundle up and go explore the beautiful Peekskill Riverfront Green Park, just steps away from the train station. This park offers some of the best Hudson River views in the entire lower Hudson Valley. Peekskill Bay is wide but the river narrows rapidly just to the north at the start of the Hudson Highlands where dramatic cliffs are picture-perfect -- especially with the Bear Mountain Bridge tucked between them. And just to the west across the river, you can see the peaks of Bear Mountain, Dunderberg Mountain, and Jones Point. This iconic view is the inspiration for the Peekskill Exurbanist logo. Peer at it through the starkly beautiful Portal sculpture for added effect.

12 pm - After exploring the river walk it's time to do some shopping -- some booze shopping. Hit up Dylan's Wine Cellar for a great selection of regional wine and spirits. Then walk over to Peekskill Brewery on Water Street and pick up some cans of locally brewed craft.

12:30 pm - It's time to head up the hill toward downtown Peekskill and the Valley Love Holiday Market. Head east up Central Avenue for about 10 minutes until you reach Bruised Apple Books on your right. This is an old-school book and record store with delightful surprises hiding around each corner. We love the small local section up front where we've found interesting books on Peekskill and Hudson Valley history. After you've browsed, continue up Central until you reach Division street and take a right. Head south until you see Peekskill's own Flatiron building. Stop in at Peekskill Coffee on the first floor to grab yourself some caffeine and maybe a cute t-shirt illustrated by one of the multi-talented baristas and then head out to Esther Street just behind the building.

1 pm - Esther Street, now known as Esther Place, is where you'll find the Valley Love Holiday Market. The small street was closed off to vehicle traffic to give the community outdoor space during the worst of the pandemic, and it has since served as a de facto town square. Explore the vendors at the holiday market, and be sure to chat with the friendly locals -- Peekskill is known as a "friendly town" after all! You can also grab a bite to eat or indulge in a warm and boozy gluhwein from The BeanRunner Cafe on the west end of Esther Place. After you've shopped with the vendors on the street, head back into the Flatiron and check out Bucko! This store is seriously cute, with a curated selection of clothing, home goods, gifts, and stuff for kids. After that head upstairs and check out the Flatiron Gallery , Winzig Art Studio, 222 Much Swag, and Lavinia Wiggins Studio for more holiday shopping.

2pm - After shopping the Market and Flatiron, it's time to shop North Division Street. First, stop at The Fern Tree and grab a unique gift sourced from African makers. The head to the Lilē & Rose Holiday Popup. This indoor Holiday pop-up will give you a chance to defrost while shopping more local vendors. After you've shopped the pop-up, walk down the street to Whiskey River for a booze break that's dripping with holiday spirit thanks to the gorgeous decorations. Then, hop across Division Street for a stop at the Quirkshop to check out the collection of handmade apparel and accessories in this quirky boutique that definitely lives up to its name.

3 pm - It's time for another booze break, this time at the cozy bar at Iron Vine! From there, head back down North Division to South Street. On South Street, you can shop for vintage 90's apparel at Stark Vintage and then visit The Rift Collectibles for comics, games, and everything for the geek in your life. Cross the street and visit Lilly of The Valley Floral Design and grab some festive holiday blooms and bouquets.

4 pm - Still thirsty? Take a walk back down to Dylan's Wine Cellar at the riverfront to partake in the last hour of their holiday wine tasting.

5 pm - If you're staying overnight, check in to one of Peekskill's hotels -- there's the luxury Abbey Inn & Spa; or the Inn on Hudson, a basic motel with killer views; or old reliable, the Holiday Inn Express. There's also plenty of Air BnB options in town.

7 pm - Dinner options are plentiful in town. If it's a chilly night, we recommend getting a hot bowl of ramen at RameNesque on Main Street. Their new dining room and sake bar is the perfect place to warm up on a cold night.

8 pm - After dinner, take in an amazing holiday show at Peekskill's own Paramount Theater and hometown hero Jessica Lynn and her amazing country-infused Very Merry Christmas Show.

10:30 pm - End the night with some drinks and live music at Birdsall House, a Peekskill institution with a vast craft beer menu and creative cocktails on demand.


8 am - Start the day with some coffee and Chilean baked goods from TerraDulce Bakery on Main Street.

9 am - Then head down to the parking lot near Peekskill Brewery to check out Westchester Cars & Coffee, a weekly showcase of some of the coolest cars in northern Westchester.

12 pm - Take a walk south along the Riverwalk until you arrive at the Factoria complex and head upstairs for brunch at Fin & Brew. The thick, fluffy pancakes are a can't miss.

1:30 pm - Head back up to Esther Place to check out Sunday's VValley Love Holiday Market vendors and wrap up the last of your holiday shopping.

4 pm - End your Peekskill weekend with a drink at the top of it all at the bar at Apropos at the Hogwarts-like  Abbey Inn & Spa. Explore the grounds and take in the epic views of Peekskill Bay and the Hudson River as you watch the sunset on a great holiday weekend in Peekskill.

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#ValleyLoveMarket Peekskill Holiday Weekend Itinerary

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