Shopping in Dutchess County worth going out for.

These 310 activities are worth leaving the house for.
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Bard Farm Stand

Bard Farm Stand

Oct. 22 & Oct. 29 at 12pm

Bard College · Annandale-On-Hudson

Stock your kitchen with veggies, herbs, and maple syrup grown by Bard students themselves. This weekly stand on a gorgeous Hudson Valley campus also carries local meat and eggs.

The Sixside Market

The Sixside Market

October 24 at 10am (This weekend) +9

The Academy · Poughkeepsie

The Sixside Market brings year-round Saturday mornings to life inside The Academy, where local farmers, bakers, and makers set up shop. It's the kind of place where you grab fresh produce, discover a new favorite candle, and actually chat with the person who grew your tomatoes.

Annual Holiday Mini Market

Annual Holiday Mini Market

November 2 at 11am

Little King · Beacon

Beacon's design-savvy crowd knows Little King as their "upstate MoMA store," and their annual Holiday Mini Market brings that same eye to artisan gifts. Browse Japanese crafts, vegan chocolates, and onigiri bentos from a handpicked lineup of vendors.

Holiday Markets and Craft Shows

Holiday Markets and Craft Shows

December 6 at 12pm

Branchwater Farms · Red Hook

Hudson Valley holiday spirit, bottled and bundled. Branchwater Farms' market brings together local makers, their own small-batch Whiskey and Gin, and a warm welcome from the folks who raise the animals and pour the tastings.

Doodle Auction

Doodle Auction

December 11 at 7:30pm

Stissing Center for Arts and Culture · Pine Plains • $10

Bid on festive doodles by local artists and celebrity creators while live music and snacks keep the mood light. A playful community evening where you might walk away with the perfect holiday gift.

Walkway Market: A Taste NY Experience

Walkway Market: A Taste NY Experience

October 24 (This weekend)

Walkway Over the Hudson State Historic Park · Highland • Free

Browse a handpicked lineup of 30 New York State makers, growers, and artisans at this open-air market. Discover local goods ranging from maple syrup and honey to handcrafted jewelry and pet treats.

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310 activities · Page 1 / 6

All activities

Thu, Oct 22 · 12:00 PM

Bard Farm Stand 12-5pm

Bard College · Annandale-On-Hudson

Fri, Oct 23 · 10:00 AM

Spellbound in the Valley

MJN Convention Center - Mid Hudson Civic Center · Poughkeepsie

$65.34

Sat, Oct 24 · 10:00 AM

Walkway Market: A Taste NY Experience

Destination Dutchess | Dutchess Tourism, Inc. · Poughkeepsie

Free

Sun, Oct 25 · 8:00 AM

Beacon Flea Market Sunday Vintage Market

Beacon Flea Market · Beacon

Sun, Oct 25 · 10:00 AM

Beacon Farmers' Market

Main Street · Beacon

Sun, Oct 25 · 10:00 AM

Beacon Farmers' Market Weekly Sunday Gathering

Beacon Farmers' Market · Beacon

Sat, Nov 7 · 8:00 AM

Stormville Airport Antique Show & Flea Market

Stormville airport · Stormville

Free

Sat, Nov 7 · 8:00 AM

Stormville Flea Market

Stormville Airport Antique Show and Flea Market · Stormville

Sat, Nov 14 · 10:00 AM

2026 Wappingers Falls Craft Fair

Wappinger Town Hall · Wappingers Falls

Sat, Nov 28 · 10:00 AM

2026 Poughkeepsie Holiday craft Fair

Dutchess Community College · Poughkeepsie

Holiday Markets and Craft Shows

Dutchess Community College · Poughkeepsie

Friends Holiday Book Sale

Poughkeepsie Public Library District - Adriance Memorial Library · Poughkeepsie

Stormville Airport Antique Show & Flew Market

Stormville Airport · Hopewell Junction

Dutchess Handmade

Gallery 40 · Poughkeepsie

Free Farm Stand

Memorial Park · Beacon

Farmers Market

Mid-Hudson Discovery Museum · Poughkeepsie

Electro-Shop Therapy

Darkside Records · Poughkeepsie

Summer & Fall Food Festivals

Dutchess County Agricultural Society Inc. | Dutchess County Fairgrounds · Rhinebeck Village

Stormville Airport Antique Show & Flea Market

Stormville Airport Antique Show and Flea Market · Stormville

Todd Hill Outdoor Market

Taste NY Market at Todd Hill · Lagrangeville

Merritt @ the Market

Millbrook Farmers' Market · Millbrook

Stanza Book Club

Stanza Books · Beacon

Holiday Bazaar

Troutbeck · Amenia

Spring Cleaning-AVRO 504 Fabric and Mixed Memorabilia Sale & Auction

Old Rhinebeck Aerodrome · Red Hook

Second Wave Supplies

Beacon

Chaseholm Farm

Pine Plains

Village Jerk

Beacon

Northwind Farms

Tivoli

Curio Cabinet of the Hudson Valley

Poughkeepsie

Wolcot Wine & Liquor

Beacon

Gather

Beacon

Loose Ends Vintage

Beacon

The Blue Olive

Pawling

Local Assortment

Beacon

Viscount Wines & Liquor

Wappingers Falls

Beacon Reads

Beacon

Rhinebeck Farmers' Market

Rhinebeck Village

Lily & Marigold Home + Design

Beacon

178-Browtique

Beacon

Walmart Supercenter

Fishkill

$

Alterniverse

Hyde Park

Friendly Lane Antiques

Hyde Park

Main Street

North East

The Rhinebeck Artist's Shop

Rhinebeck Village

Beacon Wine & Liquors

Beacon

BURKELMAN

Beacon

The Bump Boutique and Imaging

Fishkill

Rhinebeck Mercantile

Rhinebeck Village

Barb’s Butchery

Beacon

Beacon Pantry

Beacon

House of Maxx

Beacon

Rt 9 N & Mulberry St (Dutchess County Fairgrounds)

Rhinebeck Village

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Frequently asked questions

How are these shopping in Dutchess County chosen?

I go through what's actually on nearby and keep only the ones worth the trip. Nobody pays to be on this list.

Is everything here still happening?

Finished events drop off the list. Check the listing for times and booking details before heading out.

How can Outgoing help me find something I’ll actually want to do?

Tell me when you’re free, where you’ll be, and what sounds appealing. “Live music near me, somewhere I can sit, under $30” gives me more to work with than “something fun.” You can keep narrowing it down with me.

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Is Outgoing free?

Outgoing is free to use. Events have their own admission prices, including some that are free. Check the listing for prices and booking details before making plans.

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