Milestone

4.6 ( 199 reviews )
Checking... 3:00 AM - 10:00 PM See Hours
$20–30
2 Main St, Redding, CT 06896, United States
+1 203-587-1700

Milestone is a vibrant American restaurant located at 2 Main St, Redding, CT, that has quickly made a name for itself as a local favorite. Customers rave about its casual atmosphere, highlighted by friendly service and an engaging environment perfect for gatherings. As Seamus McEvoy points out, the wings and fennel sausage platter are popular picks, complemented by a fun night of live music—an experience many guests can't resist.

Thursdays are particularly special with half-priced wine bottles, making it an ideal time to enjoy their delicious Beet appetizer, as noted by Sholom Ellenberg. The generous portions are a key highlight, as echoed by Mark Hanze, along with the cozy ambiance featuring a fire pit—perfect for cool summer nights.

Whether you're indulging in their famously good burgers or enjoying the attentive service from waitstaff like Shannon and her diligent team, diners agree that Milestone not only serves satisfying dishes but also creates memorable experiences. With a combination of great food, a lively atmosphere, and thoughtful service, Milestone is a must-visit venue in Redding that ensures every night out feels like a special occasion.

Amenities and More

  • Accessibility
    • Has wheelchair-accessible car park
    • Has wheelchair-accessible entrance
    • Has wheelchair-accessible seating
    • Has wheelchair-accessible toilet
  • Service options
    • Has outdoor seating
    • Offers delivery
    • Offers takeaway
    • Serves dine-in
  • Highlights
    • Has fast service
    • Has great beer selection
    • Serves great cocktails
    • Serves great dessert
    • Has great wine list
    • Has live music
    • Good for watching sport
  • Popular for
    • Popular for dinner
    • Good for solo dining
  • Offerings
    • Serves alcohol
    • Serves beer
    • Serves cocktails
    • Serves coffee
    • Serves comfort food
    • Serves food
    • Serves happy-hour drinks
    • Serves happy-hour food
    • Serves healthy options
    • Serves organic dishes
    • Serves small plates
    • Serves spirits
    • Serves wine
  • Dining options
    • Serves breakfast
    • Serves brunch
    • Serves dinner
    • Serves dessert
    • Has seating
  • Amenities
    • Has bar on site
    • Has toilet
    • Has Wi-Fi
    • Free Wi-Fi
  • Atmosphere
    • Casual
    • Cosy
    • Trendy
  • Crowd
    • Family friendly
    • Good for groups
    • Popular with tourists
  • Planning
    • Accepts reservations
  • Payments
    • Accepts credit cards
    • Accepts debit cards
    • Accepts NFC mobile payments
    • Credit cards
  • Children
    • Good for kids
    • High chairs available
    • Has kids' menu
  • Parking
    • Free of charge street parking
    • Free parking lot
    • Plenty of parking

Reviews For Milestone

Seamus McEvoy
Jun 22,2025
Yes. Very good. Casual atmosphere, and full of people that just want to have fun. I can highly recommend their wings, the fennel sausage platter (killer pickled veg) and their burger. The drinks flowed, Drew took very good cate of us, and the band rocked. Awesome night. We will be back.
Sholom Ellenberg
May 25,2025
Great experience. Food was delicious and we had a great night to sit outside. We took advantage of half price wine bottles on Thursday night! Also don't miss the Beet appetizer, yummy.
Mark Hanze (Mix Master Mark)
May 15,2025
Great portions, very friendly service, and a fantastic atmosphere. Enjoy the fire pit on cool summer nights
Susan S
May 11,2025
We had the best time here last weekend! Service was great (I think Shannon was our servers name), drinks awesome, great burger and one of the best Caesars around!
Dory McLaughlin
May 2,2025
Lovely waitress - I wish I could remember her name, but she was killing it. My sister and I could tell they were short staffed and everyone was absolutely busting their butts off. I only wish that the people enjoying the restaurant treated the staff with more kindness and compassion for how hard they were working. The food and drinks were good and the restaurant was beautiful.
Jim McCarthy
Apr 20,2025
My wife and I had a very nice dinner at Milestone last night. I had the “Devils Eggs” as an appetizer and the hangar steak with chimichura sauce as the main course. Both were delicious. Nice bourbon selection, too. It’s family friendly, service was excellent and, overall, a nice experience. We’ll be back!
Marian Sawyer, ASCAP
Mar 14,2025
A very charming and spacious local Georgetown, Weston restaurant featuring a very large wood fired pizza oven. Extremely comfortable with a relaxing reading
Adeline Fusco
Mar 11,2025
This is my go-to local bar. They have live music almost every Saturday (in the warm months, outside on an actual stage, which is great!) Food is good; a bit expensive, I'd say, for the area. Excellent cocktail menu because they actually invested in a bar program. Gets super busy at early dinner time, with tons of kids, so I tend to avoid it then. Prefer the evenings, which are also crowded, but more of a party-vibe.

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