As part of Massachusetts tradition, the Hyannis Father’s Day Car Show is an hour and a half outside the city—but worth the trip. Thousands of auto fans come out to see vintage automobiles of all types. Stick around for awards and other fun features at this one-day-only event, perfect for enthusiasts. Classic hot rods are out on show 8:30 a.m.–2 p.m.

Watching a live sporting event is always superior to watching television. This Father’s Day, catch a beautiful afternoon at the ballpark and watch the Boston Red Sox take on the New York Yankees in a rivalry for the ages. Fenway Park is the historic outpost for watching sports in Boston, with close access to Kenmore Square and several other points of interest.

The game starts on Sunday, June 16, at 7:10 p.m. EST.

For dads who love to puff, invest in a one-of-a-kind cigar experience. Throughout Boston, find several esteemed smoking lounges, each with its backstory and selections. Once a speakeasy, Stanza Dei Sigari holds many rustic charms, from rich leather upholstery to wooden details and a dark, inviting demeanor. Indulge in a cigar-spirit pairing and take a few sticks home for Dad to store in a humidor for your next cigar night.

Don’t forget to check out other cigar lounges in Boston, such as vintage Lucky’s Lounge or the historical hideaway L.J. Peretti Co.

While spending hours shopping might be mom’s preferred activity versus dad’s, many fathers will delight in scouting out excellent leather goods to add to their wardrobe staples. Since these personal items require extra thought, it’s best to make shopping for Dad a joint effort. Stores at Faneuil Hall carry handcrafted wallets, briefcases, shoes, and other commodities that make excellent gifts. Two specialty shops include The Leather Shop, an expansive gift selection, and the nearby Helen’s for luxe wares with Western flair.

Faneuil Hall is open 11 a.m.–7 p.m. on Sunday.

Boston’s waterfront is essential to any city outing, and sea-loving dads will adore making a thoughtful memory here. The harbor offers a variety of water experiences, from whale-watching to sightseeing and sunset viewing.

Dads and beers are a classic pair, and Night Shift Brewing Kitchen & Tap at Encore Boston Harbor is the ideal setting to kick back with some brews. Go for the Local Luck and a pretzel, or nosh on chips and dip with a Lime Lite before diving into some beer-compatible comfort food. Since Night Shift is a weekender’s dream, stop in on the Friday and Saturday before Father’s Day to try the vast selections.

Father’s Day is the time for dad to have their favorite meal. Steak tops most lists when it comes to a decadent dinner. Rare Steakhouse features a raw bar and caviar service that will delight seafood lovers, and the Wagyu splurge is the crown jewel.

On Father’s Day, treat dad to a Rare occasion 5–10 p.m. on Sunday, June 16.

June is prime time for impeccable weather. If your dad loves the great outdoors, numerous trails and nature experiences close to Boston are prime for a Sunday outing.

Depending on travel time, there are several hiking spots from which to choose. The Middlesex Fells Reservation is a premium area with challenging trails that capture photo-worthy views from stunning vantage points. The Breakheart Reservation allows for walking, running, and biking, while a deep exploration of the Harold Parker State Forest might be a recipe for Father’s Day success.

For the guys who love athleisure, now is the time to stock up on golf fits and pickleball essentials. Wynn Sports features designer brands that sporty dads love to be gifted with. Whether dad is a Boston fan or a Wynn devotee, find the perfect gifts for his personality.

Wynn Sports is open Sunday from 12–7 p.m. for Father’s Day. You can purchase retail goods with COMPDOLLARS.

As part of Massachusetts tradition, the Hyannis Father’s Day Car Show is an hour and a half outside the city—but worth the trip. Thousands of auto fans come out to see vintage automobiles of all types. Stick around for awards and other fun features at this one-day-only event, perfect for enthusiasts. Classic hot rods are out on show 8:30 a.m.–2 p.m.