It’s day trip season — the time to roam around our towns and countrysides. You’ll inevitably get hungry, though, so before spending 30 minutes scrolling to find a good place to eat, here are some recommendations for irresistible sandwiches across the hills of Berkshire, Litchfield, Columbia, and Dutchess counties. This list includes hole-in-the-wall joints, fancy bistros, and everything in between, plus some of my everlasting favorites as a long-term local.

Berkshire County
When I asked South County folks about their favorite sandwiches on social media, around a dozen people mentioned Taft Farms in Great Barrington, which has an epic deli counter. The Bully Boar was mentioned specifically — a roast beef sandwich with bacon, pepper jack, lettuce, tomato, and mayo. There’s also the Seoul Reuben, which comes with local kimchi and Indonesian sweet soy sauce.

To the north, seek out The Daily Grind. It’s generous, inexpensive, and right in the middle of downtown Adams, which is full of new activity these days and in great proximity to the Ashuwillitcook Rail Trail. My favorite is the Mailman, which is made with turkey, bacon, and coleslaw. They wrap it up nice and tight so you can take it to go.

Farther south, don’t miss Berkshire Mountain Bakery in Pittsfield, which has renowned bread and an amazing portobello sandwich with sun-dried tomato pesto, mozzarella, and balsamic glaze.

Columbia County
In New Lebanon, Blueberry Hill Market and Cafe is a must-eat, if you can get in; it’s been packed since it opened a little over a decade ago. The Southwest Burger is a highlight for vegetarians — an excellent veggie burger with cheddar, avocado, pickled onion, and chipotle mayo on challah. Chatham’s Our Daily Bread — both the full-service restaurant and the gluten-free spot on the other end of town — also has an excellent veggie burger, if you’re looking.

Litchfield County
In Kent, Wilson’s is a fixture; it’s a full-service bakery and cafe, and its sandwich options are like nowhere else. Get a simple prosciutto baguette or go wild with a prime rib sandwich with caramelized onion and horseradish cheddar aioli; if you’re off red meat, get a pulled pork sandwich with blueberry BBQ sauce or an open-faced pork belly chashu.

In college, I spent many happy summers gardening for summer residents all over Litchfield, and I loved stopping at The Bridgewater Village Store and Bistro, which is still open today (although it’s under new ownership). Get the Righteous Grilled Cheese, which combines gruyere, cheddar, Manchego, fontina, and goat cheese on sourdough.

The Pantry in Washington Depot is also a classic spot (open since 1977), with a menu updated daily and special touches like homemade sauerkraut and house-roasted meats.

Northern Dutchess
In Rhinebeck, Aba’s Falafel is serving up flawless, classic Mediterranean fare, with a falafel-in-pita situation that’s perfect for walking around or sitting outside. If you want to be really wowed, get a sabich pita, with roasted eggplant, potato, falafel, lettuce, tahini, and mango curry sauce.

Alimentari Rossi and Sons in Poughkeepsie is the quintessential Italian deli, with top-notch sandwiches, pastries, and antipasti. The Smoky Giuseppe is the one to get, with fried eggplant, provolone, mozzarella, nduja, smoky eggplant spread, roasted pepper, tomato confit, prosciutto, and stuzzichino. How could you resist such a considered combo?

If you’re in Millbrook, Babette’s Kitchen is a great place for a quick bite. Try the smoked salmon BLT — and don’t skip the soup, which is always on point.

Honorable Mention: Reubens
People mentioned reubens time and time again when I asked this question in various local social media groups. The Frog in Sheffield, The Store at Five Corners in Williamstown, The Great Barrington Bagel Co., and the Olde School Deli in Canaan, Connecticut all got multiple mentions in the reuben category.

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Written by
Francesca Olsen