What to Do in Brewster: How to Spend a Winter Day in Town

In Putnam County, Brewster delights with snow sports fun on the mountain or the rink, a famous burger shack, and jazzy nightlife.

On the hunt for mountain fun closer to Westchester or Connecticut? Brewster is the day trip town you need to check out this winter. The Putnam County destination offers so many things to do to keep you active all day long without the cold weather weighing you down. Along with snow sports, Brewster is home to a bustling culinary scene, including a historic burger shack, authentic Mexican eats, and a boozy jazz bar.

Here’s your guide to an ideal winter day in the historic town. Heading there soon? Tag us @hudsonvalleymag on Instagram if you visit any of the destinations in our guide.

9:30 a.m. – Grab a mid-morning brunch at Country Kitchen Restaurant

 

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Sleep in a bit before kicking off your day trip with a big brunch at Country Kitchen Restaurant. Located in the center of town on North Main Street, the cozy spot serves up breakfast, lunch, and dinner with the same signature culinary flair. Enjoy your pick of caffeinated beverage, from lattes to ice coffees, and pair it with a country skillet or specialty French toast for a savory or sweet option. While the crazy loaded tots are a must for the table to share, you’ll want to keep the dulce de leche French toast or country Benedict all to yourself.

564 North Main Street, Brewster
845.279.8646

11 a.m. – Enjoy a winter walk on the Putnam Trailway

brewster
Photo by Kayla Sexton

After breakfast, bundle up for a scenic winter walk on the Putnam Trailway. A section of the Empire State Trail, the trailway runs for nine miles from Mahopac to Brewster with waterside views and woodland scenes the whole way. No matter where you start your journey on the path, you’re sure to see landscapes of the Middle Branch Reservoir or Lake Tonetta, along with winter wildlife and a few snowflakes if you’re lucky.

Multiple entry points in Brewster

12:30 p.m. – Refuel with burgers at the historic Red Rooster Drive-In

 

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Ever wondered what it was like to dine at a drive-in during the 1960s? Head to Brewster’s historic Red Rooster Drive-In to find out. The iconic red and white striped building on Route 22 first opened its doors in 1963 as a simple custard stand. After many evolutions, the very same building is still standing with even more options than before, from classic burgers and hotdogs to veggie burgers, salads, and, of course, ice cream. Grab a quick bite here and make a mental note to revisit the spot in the warmer months for miniature golf right next to the burger shack.

1566 Route 22, Brewster
845.279.8046

2 p.m. – Hit the slopes at Thunder Ridge Ski Area

Moving on to the main event of the day, gear up to hit the slopes at Thunder Ridge Ski Area, located just up Route 22 in Patterson. The ski mountain is the perfect place for family-friendly fun, with 22 trails, three chairlifts, four magic carpets, gentle slopes for beginners, and advanced trails for the adventurous. Lift tickets are only $50 on weekdays and $73 on weekends, with discounts for seniors and younger skiers and boarders. While Thunder Ridge has its own fully stocked ski shop, stop at Ski Haus on the way over for smaller lines and rentals before you get to the mountain.

137 Birch Hill Road, Patterson
845.878.4100

4 p.m. – Have a late-afternoon skate at the Brewster Ice Arena

 

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If skiing and snowboarding isn’t enough winter fun for you, cut your mountain adventures a little short to stop by the Brewster Ice Arena. The ice-skating destination features two full ice-skating rinks, a studio rink, and an outdoor pond in the colder months. Rent a pair of skates for just $4 or bring your own to get out on the ice or look into the public figure skating and open hockey options if you’re more advanced. When things get too cold, stop by the concession for a hot chocolate.

63 Fields Lane, Brewster
845.279.2229

6 p.m. – Dig into authentic Mexican dishes at Las Mañanitas

As large as this restaurant is, Las Mananitas is packed on all four of its levels during the warmer months – partly for the dazzling views of the East Branch Reservoir, but mostly for the authentic cuisine. Luckily, a winter visit means getting a table immediately to indulge in some of the best mojitos and margaritas you can find in the Valley. Make sure to order guacamole for the table and specify mild, medium, or hot, then sit back and enjoy the show as your waiter brings all the guacamole fixings over to you and whips it up fresh in a molcajete before serving it with homemade tortilla chips.

When it comes to the menu, there isn’t something you could order that wouldn’t have you bookmarking this restaurant for your next celebratory dinner. From the Tradicionales to the Del Mar, the options for a delicious Mexican meal are endless. The menu even has a section titled Vegetarianos filled with vegetable-based dishes that will blow your mind. You’ll want to order the Mexican coffee at the end of the meal for a flaming hot dessert (literally).

1250 Route 22, Brewster
845.279.4646

6 p.m. – Or savor farm-to-table fare at Clock Tower Grill

Alternatively, if you’re not feeling Mexican for dinner, try Brewster’s Clock Tower Grill for farm-to-table fare. Since 2013, the husband-and-wife-led restaurant has been serving up creative dishes made with ingredients from local farms, including from the couple’s own farm in Connecticut. The seasonal menu changes throughout the year, offering dishes ranging from tuna cones to house-made pastas to roast duck. For an even more exciting culinary experience, choose the Eat Like a Chef option to enjoy a family-style feast at $100 per person.

512 Clock Tower Drive, Brewster
845.582.0574

8 p.m. – Catch a jazz show and grab drinks at Uncle Cheef

 

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Once you’ve had your fill of Mexican food, pay a visit to Uncle Cheef for live music from Thursday through Sunday. Owned by Tonight Show musician and six-time Grammy Award-winning saxophonist Ian Hendrickson-Smith, you know this bar is going to be a good time with music curated by Hendrickson-Smith himself. Sit down at one of the moody tables or head to the chic bar and order a classic cocktail or a seasonal specialty like the Figgy Gillespie or the Sage Against the Machine to sip while you enjoy live jazz and more good tunes.

988 Route 22, Brewster
845.793.2717

10 p.m. – Turn in for the night at Heidi’s Inn

After your long day of winter activities, settle in for the night in the cozy Heidi’s Inn. With fair rates and newly renovated rooms, the inn is the perfect place to rest your head once you’re tired out from so many exciting events. Each room has kitchen amenities like a microwave and refrigerator in case you have any leftovers, and free breakfast and Wi-Fi are included in your stay.

1270 Route 22, Brewster
845.279.8011

Related: What to Do in Poughkeepsie: The Best Way to Spend a Day in Town

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