As promised, here are our Fall 2026 dress-up night ideas.

We searched across Connecticut for great ways to enjoy an evening out. This guide supplements the Kingdom Marriage Retreat and is open to everyone—couples, friends, family members, and groups.

Pick a show, choose dinner, make a reservation, or use the list as inspiration to find your own night out. Several options include gluten-free planning notes; confirm accommodations directly before booking.

Shows + Dinner Dining Experiences

Shows With Dinner

Dress up, enjoy dinner, and make a night of it. Performance dates reflect the Fall 2026 schedules included in the GTM guide.

Sept. 29–Oct. 4

The Great Gatsby

VenueThe Bushnell, Hartford
DinnerMax Downtown
AttireCocktail or formal
Gluten-FreeMax has gluten-free selections; mention the restriction when reserving.
Budget for Two$350–$600
Oct. 1–4

The Wiz

VenueShubert Theatre, New Haven
DinnerUnion League Café
AttireCocktail
Gluten-FreeCall ahead to arrange accommodations.
Budget for Two$325–$550
Oct. 2–4

Mystic Pizza: A New Musical

VenuePalace Theater, Waterbury
DinnerDiorio’s or pre-show dining at the Poli Club
AttireCocktail
Gluten-FreeRequest gluten-free preparation in advance.
Budget for Two$250–$450
Oct. 2–4

New World Symphony & Beyond

VenueThe Bushnell, Hartford
DinnerMax Downtown or The Capital Grille
AttireCocktail or formal
Gluten-FreeBoth restaurants can accommodate dietary requests with notice.
Budget for Two$250–$450
Oct. 10

Nrityagram Dance Ensemble

VenueShubert Theatre, New Haven
DinnerUnion League Café
AttireCocktail
Gluten-FreeCall ahead before reserving.
Budget for Two$250–$425
Oct. 16

Michael Carbonaro: WONDERBOY

VenueShubert Theatre, New Haven
DinnerUnion League Café
AttireCocktail
Gluten-FreeCall ahead before reserving.
Budget for Two$250–$425
Oct. 20–25

Mamma Mia!

VenueThe Bushnell, Hartford
DinnerMax Downtown or The Capital Grille
AttireCocktail
Gluten-FreeMention the restriction when reserving.
Budget for Two$350–$575
Oct. 23–25

Dinur Conducts Tchaikovsky 4

VenueThe Bushnell, Hartford
DinnerMax Downtown or The Capital Grille
AttireCocktail or formal
Gluten-FreeMention the restriction when reserving.
Budget for Two$250–$450
Oct. 30–Dec. 27

Annie

VenueGoodspeed Opera House, East Haddam
DinnerGelston House
AttireCocktail
Gluten-FreeConfirm available gluten-free entrées when reserving.
Budget for Two$275–$475
Nov. 7

American Ballet Theatre Studio Company

VenueShubert Theatre, New Haven
DinnerUnion League Café
AttireCocktail or formal
Gluten-FreeCall ahead before reserving.
Budget for Two$250–$450
Nov. 10–15

BOOP! The Musical

VenueThe Bushnell, Hartford
DinnerMax Downtown
AttireCocktail
Gluten-FreeMax has gluten-free selections; mention the restriction when reserving.
Budget for Two$350–$550
Nov. 18–22

How the Grinch Stole Christmas! The Musical

VenueShubert Theatre, New Haven
DinnerUnion League Café
AttireCocktail or festive formal
Gluten-FreeCall ahead before reserving.
Budget for Two$300–$500
Planning note: Max Downtown, Union League Café, Gelston House, and Diorio’s publish current menus online. Max Downtown also provides complimentary parking in its attached garage.

Standalone Dining Experiences

No show required. These are full-evening experiences built around the meal itself.

Essex

Essex Clipper Dinner Train

ExperienceApproximately 2½-hour train ride and four-course dinner in restored Pullman dining cars
AvailabilityScheduled dates throughout the year; fall dates should be booked early
AttireCocktail
Gluten-FreeDietary needs must be confirmed before purchasing
Budget for Two$240–$325
Cheshire

Newbrook Kitchen Supper Club

ExperienceSix-course supper club with an open-kitchen view; approximately 2–2½ hours
AvailabilityReservation-only monthly events
AttireDressy
Gluten-FreeEntire supper-club menu is 100% gluten-free
Budget for Two$190–$220
Old Saybrook

The Essex Chef’s Tasting

ExperienceAmuse-bouche, canapés, five courses, pre-dessert, dessert and mignardises
AvailabilityTuesday through Saturday evenings
AttireCocktail
Gluten-FreeCall ahead; the restaurant may not be able to modify the menu at the last minute
Budget for Two$275–$325
Tariffville

Present Company Tasting Menu

ExperienceFive-course chef’s tasting menu
AvailabilityOffered regularly by reservation
AttireCocktail
Gluten-FreeDietary restrictions should be discussed before booking
Budget for Two$325–$400
Morris

The Restaurant at Winvian Farm

ExperienceLuxury seasonal prix-fixe fine dining in the Litchfield Hills
AvailabilityDinner Tuesday through Sunday; reservations required
AttireCocktail or formal
Gluten-FreeDiscuss restrictions directly with the restaurant
Budget for Two$375–$450
Simsbury

Millwright’s Chef’s Tasting

ExperienceChef-driven tasting experience in a historic mill overlooking a waterfall
AvailabilityYear-round by reservation
AttireCocktail
Gluten-FreeThe restaurant requests advance notice of allergies and restrictions
Budget for Two$225–$350
The Essex Clipper serves a four-course meal aboard restored 1920s dining cars. Newbrook Kitchen’s supper club is entirely gluten-free. The Essex and Present Company offer chef’s tasting experiences, while Winvian and Millwright’s provide reservation-based fine dining options.

Helpful Links

Schedules, pricing, menus, and dietary accommodations can change. Confirm details directly with each venue before booking.

Overview Fall Dress Up Event Ideas in CT