3 min read

Best Golf Weekend Trips from Boston

Carl's take

Build a golf weekend around confirmed rounds, then book the beds. Keep the second course near the first and leave room for weather. A trip with less driving usually leaves more time for the reason you're going.

A road ribbon weaving through a coastal dune, mountain ridge and pine grove
Original editorial illustration; not a photograph of the course.

Greater Boston golf guides

Book the anchor round first

Pick the round everyone is traveling for, then arrange the room and a second nearby course. A Plymouth day, a Cape weekend and an Aquidneck Island trip have different budgets and routes. Do not make the second round a long transfer across the region.

Pinehills

From May 2 through October 18, 2026, either Pinehills course costs $140 Monday–Thursday or $175 Friday–Sunday. After 2:30pm, those rates are $100 and $115. A cart and range balls are included. Spring and late-autumn rates differ; check the date-specific rate card.

Regular online reservations open ten days ahead at midnight; same-day bookings are by phone. Limited advance weekend reservations require prepayment. Cancel at least 24 hours ahead.

Waverly Oaks

Prime-season May–October 18-hole rates are $110 Monday–Thursday and $145 Friday–Sunday, with a GPS cart and range balls included. Twilight is $90 or $110 and does not guarantee 18 holes. Carts must return 15 minutes before sunset.

Changes and cancellations are free until 24 hours before play; the group owes payment for late cancellations and no-shows. The separate group advance-booking program has its own prepayment and fee terms.

The Captains

September 8–October 12, 2026 morning fees before 1pm are $72 Monday–Thursday and $93 Friday–Sunday and Columbus Day. October 13–25 morning fees are $58 or $69; October 26–December 31 lists $50 before 1pm. Carts add $26 per rider.

Use The Captains’ official reservation link for Port or Starboard. Its current seasonal card has separate start-time bands; check the date and course before paying.

golf bags being lifted into a hatchback alongside a small weekend duffel
Photo illustration: golf bags being lifted into a hatchback alongside a small weekend duffel.

Cranberry Valley

The 2026 card lists $90 Monday–Thursday May 26–August 27 and $90 Friday–Sunday and holidays May 8–October 12. October weekday fees are $50; October twilight begins after 2:30pm at $35. An 18-hole cart adds $26 per person.

Use Cranberry Valley’s official booking link and current tee-time allocation rules. Twilight timing changes with the season; the summer after-4pm offer is not the October window.

Triggs

The 2026 walking fees for 18 are $55 weekday and $65 weekend; nine holes is $32 or $35. Carts add $22 for 18 or $12 for nine. The after-5pm twilight offer is $24 walking or $34 riding, first-come, first-served.

Ordinary reservations open seven days ahead, with no single-player bookings. Cancel at least 24 hours ahead. Some pass categories have a shorter three-day window.

Newport National

The Orchard Course’s May 21–September 26, 2026 fees are $210 Monday–Wednesday and $235 Thursday–Sunday and holidays, with a cart. September 27–November 28 fees are $160 and $185. The separate Vineyard nine has its own rate card.

The published online window is seven days and cancellations need 72 hours of notice. Check-in is at 425 Mitchell’s Lane. Children under 12 and non-playing ride-along guests are not allowed on the course.

Leave space between commitments

Allow for the journey, check-in and a round that runs later than planned. If you want 36 holes, confirm replay or second-round access with the operators. A twilight fee does not establish that you can complete the second 18.

Sources and current booking information

Reviewed October 6, 2026. Prices and access can change; use the operator's terms for your date.

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Frequently asked questions

Should I book the golf or the room first for a weekend trip?

Pick the round everyone is traveling for, then arrange the room and a second nearby course. A Plymouth day, a Cape weekend and an Aquidneck Island trip have different budgets and routes. Do not make the second round a long transfer across the region.

Carl Golf

Carl helps golfers compare supported public tee sheets by text in Greater Boston and Phoenix & Scottsdale. Our guides use operator sources for rates and access. Questions or feedback: hello@carl.golf

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