Before our daughter was born, my husband and I had a good habit of getting out of the house and exploring restaurants in Boston. With a variety of cuisines in our neighborhood plus a child-free lifestyle, date nights were easy.

With a move to the suburbs, a pandemic, and a new addition to the family, date night fell lower on the priority list. It quickly became clear that our relationship desperately needed one-on-one connection — outside of our home. Restarting our commitment to date night was just the thing we needed.

After jumping through the hurdle of finding a babysitter, we committed ourselves to exploring a new restaurant in our MetroWest community once a month. If you’re a fellow MetroWest mom on the lookout for new date night restaurants, here are a variety of delicious options just waiting for you to try!

Buttercup :: Natick

A delightful farm-to-table American cuisine restaurant in the heart of downtown Natick, Buttercup is an absolute joy for date night. Mason jar candles and chic barn wood aesthetics create the perfect environment to reconnect with loved ones over a bottle of wine or appetizer. Chef and co-owner Dora Tavel-Sanchez Luz is a mother of two and multi-year Boston Marathon runner, and she delivers fresh seasonal menus that make it easy to return over and over. Reservations are a must!

Juniper :: Wellesley

Self-described as a quasi-Mediterranean restaurant, Juniper is the perfect place to give your tastebuds a tour. The muhammara with housemade pita is a must. Travel to Morocco with the chicken tagine or to Iran with the ghalieh mahi (seafood stew). End the evening by splitting the warm date cake — what a delightful date night!

Oak Barrel Tavern :: Sudbury

With a rustic tavern feel, an extensive drink menu, and multiple gluten-free options, Oak Barrel Tavern is the place for a hearty meal. Enjoy burgers, steak tips, and a seasonal cocktail. With both tables and a bar for watching the game, the ambiance can be a bit louder, giving you the air space to laugh with your partner at the latest antics of your tiny, irrational humans.

The Oregon Club :: Ashland

Founded in 1922 as a rooming house that doubled as a speakeasy, The Oregon Club turned into a private club during prohibition in the 1930s. Today, this Ashland gem continues its 100-year tradition. Now run by a husband-wife team, this “odd little farmhouse” makes you feel like you are dining in the comfort of your home and offers a small but mighty menu of dishes, including “The Steak.” Outdoor seating is a noted bonus. Reservations are required.

Giacomo’s Ristorante :: Wayland

Offering a taste of the North End in MetroWest, Giacomo’s Wayland is the sister restaurant to Giacomo’s in Boston. With an extensive wine list and an even longer menu of Italian staples, you can’t go wrong if you are in the mood for a good pasta dish. The garlic bread is a must. Reservations are strongly recommended for Friday and Saturday nights.

Avenue :: Medfield

Nestle into a cozy booth with hints of burning wood wafting through the air at Avenue. With wood fire being the primary cooking method for many of the menu items, chef and owner Joshua Foley knocks it out of the park. Noted for its outstanding service, Avenue is the perfect location to try a few appetizers and split an entree — and be sure to leave room for dessert! Reservations are required.

Looking for other date-night restaurants nearby? Check out these 10 restaurants north of Boston, these eight restaurants in the Boston area, and these nine restaurants on Boston’s South Shore!


Sarah Aspinwall
Sarah grew up in Connecticut, but Massachusetts has always felt like a second home with extended family across the state. With a master's in public health and a lifelong passion for healthcare, Sarah moved to Boston after graduation. She is a fierce advocate for better access and reducing the complexities of the healthcare system. Sarah met her husband covered in sweat and lifting weights at a local CrossFit gym (talk about first impressions!). They adopted a rescue pup from Mississippi and welcomed their daughter in 2021. After nearly a decade of city living, Sarah and her family headed to the Metro West area to start a new adventure in the suburbs. Sarah has volunteered for Community Consulting Teams of Boston (CCT), offering pro bono management consulting to Boston-area nonprofits, and she served a three-year term on the board. She is an alumna member of the Kappa Delta sorority and has served as an advisor to the Northeastern chapter since 2014.