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October 20, 2023
Poughkeepsie, NY

Paige & Tim

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    Things To Do

Things To Do

Mill House Brewing Company

289 Mill Street, Poughkeepsie, NY 12601

A great local spot where we've enjoyed many good brews and shared lots of laughs with friends and family!

Walkway Over the Hudson

61 Parker Avenue, Poughkeepsie, NY 12601

The Walkway Over the Hudson, formerly the Poughkeepsie Railroad Bridge, is the longest elevated pedestrian bridge! The walkway and adjacent parks host great facilities and accessible parking. The views you'll see while taking a stroll across the walkway on a beautiful fall day will not disappoint!

DuBois Farms

209 Perkinsville Road, Highland, NY 12528

For the quintessential NY fall experience head over to Dubois Farms for Pick-Your-Own Strawberries, Nectarines, Plums, Apples, Peaches, Flowers, and more. Their bakery has delicious desserts, including homemade apple cider donuts, served warm, and assorted handmade pies. The Tavern also has a variety of the best local hard cider, craft beer and wine.

Main Street in Beacon

Main Street, Beacon, NY 12508

Settled in 1708 and established in 1913 on the banks of the Hudson River at the foot of Mt. Beacon and Fishkill Ridge, Beacon had grown into a busy and bustling river city filled with and eclectic mix of shops, eateries, small businesses, and creatives.

Main Street in New Paltz

Main Street, New Paltz, NY

One of the best things to do in New Paltz is take a walk downtown stopping in a few of the small, independent shops, restaurants, cafes, and galleries here. Right around the corner is the historic Huguenot Street for a glimpse of colonial American history.

TR Gallo Waterfront Park in Kingston

30 Rondout Landing, Kingston, NY 12401

Kingston, New York’s historic waterfront district is a vibrant and constantly evolving neighborhood. Antique dealers, chefs, and artists have moved into “The Rondout” alongside existing waterfront restaurants, museums and commercial retail establishments, creating a destination known for art, antiques, food, and culture.

Stockade District in Kingston

Kingston, NY 12401

Uptown Kingston’s historic Stockade District is an eight-block attraction that’s equal parts colonial-era time capsule and bustling retail enclave. Some of our favorite spots are Rough Draft, Kingston Consignments, Half Moon Books, and Hill Valley Candles!

Tinker Street in Woodstock

Tinker Street, Woodstock, NY 12498

Tinker Street is a great shopping and dining area in Woodstock! There’s so much art and music in this town that makes it a wonderful place to explore.

Burger Hill

3158 New York 9G, Rhinebeck, NY 12572

Burger Hill is just a short walk from the trailhead parking lot. This special spot is where Tim popped the question in August 2021!

For all the days along the way
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